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Các hợp chất dị vòng thơm như oxazole, imidazole, thiazole…đang nhận được rất nhiều sự quan tâm nghiên cứu của các nhà khoa học vì những ứng dụng của chúng trong các ngành sản xuất như: hóa dược, phẩm nhuộm… Ngoài ra nó còn được ứng dụng trong các hợp chất có hoạt tính sinh học… Trong số đó thì dị vòng thiazole tỏ ra là một trung tâm mang... Đề tài Hoàn thiện công tác quản trị nhân sự tại Công ty TNHH Mộc Khải Tuyên được nghiên cứu nhằm giúp công ty TNHH Mộc Khải Tuyên làm rõ được thực trạng công tác quản trị nhân sự trong công ty như thế nào từ đó đề ra các giải pháp giúp công ty hoàn thiện công tác quản trị nhân sự tốt hơn trong thời gian tới.
BỘ GIÁO DỤC ĐÀO TẠO TRƯỜNG ĐẠI HỌC SƯ PHẠM THÀNH PHỐ HỒ CHÍ MINH KHOA HĨA HỌC * * KHÓA LUẬN TỐT NGHIỆP CỬ NHÂN HÓA HỌC Chuyên ngành: Hóa hữu ĐỀ TÀI 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca Người thực : Nguyễn Văn Lốc e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 Niên khóa : 2008-2012 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 Tp Hồ Chí Minh 5-2012 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 BỘ GIÁO DỤC ĐÀO TẠO TRƯỜNG ĐẠI HỌC SƯ PHẠM THÀNH PHỐ HỒ CHÍ MINH KHOA HĨA HỌC * * KHĨA LUẬN TỐT NGHIỆP CỬ NHÂN HĨA HỌC Chun ngành: Hóa hữu ĐỀ TÀI 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b Người hướng dẫn khoa học: ThS Lê Thị Thu Hương dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca TS Nguyễn Tiến Công e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b Người thực : Nguyễn Văn Lốc fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 Niên khóa : 2008-2012 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Tp Hồ Chí Minh 5-2012 LỜI CẢM ƠN Để hồn thành tốt khóa luận này, tơi xin gửi đến cô Lê Thị Thu Hương thầy Nguyễn Tiến Công - người thầy - người hướng khoa học - người khuyến khích động viên cho tơi lời khuyên quý báu suốt thời gian thực khóa luận - lời cảm ơn chân thành sâu sắc Ngồi tơi xin chân thành cảm ơn đến Nhà trường, Khoa Hóa Học, thầy phịng thí nghiệm, thầy khoa Hóa giúp đỡ tơi hồn thành khóa luận suốt thời gian thực phịng thí nghiệm Cuối gia đình, bạn bè - người thân ln ln động viên, giúp đỡ tơi thời gian qua Vì thời gian có hạn, chưa có kinh nghiệm, nên khóa luận khơng tránh khỏi thiếu sót Tơi mong nhận ý kiến đóng góp từ q thầy bạn, để khóa luận hoàn thiện Xin chân thành cảm ơn! Thành phố Hồ Chí Minh tháng năm 2012 Sinh viên 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a Nguyễn Văn Lốc 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 MỤC LỤC LỜI MỞ ĐẦU CHƯƠNG I : TỔNG QUAN I GIỚI THIỆU CHUNG VỀ DỊ VÒNG THIAZOLE Vài nét cấu tạo Tính chất .9 II PHƯƠNG PHÁP TỔNG HỢP MỘT SỐ HỢP CHẤT CHỨA DỊ VÒNG THIAZOLE 10 Phương pháp đóng vịng gián tiếp thơng qua hợp chất α-halocarbonyl (phương pháp Hantzsch) 10 Phương pháp đóng vịng trực tiếp 14 III ỨNG DỤNG CỦA DỊ VÒNG THIAZOLE VÀ DẪN XUẤT 15 SƠ ĐỒ TỔNG HỢP .26 I II THỰC NGHIỆM 26 Tổng hợp 5-bromo-2-hydroxybenzaldehyde (1) 26 Tổng hợp 5-bromo-2-hydroxybenzandehyde thiosemicarbazone (2) 27 Tổng hợp 4-bromo-2-{[2-(4-phenyl-1,3-thiazol-2-yl)hydrazinylidene] methyl} (3a) .27 Tổng hợp 4-bromo-2-[{2-[4-(4-bromophenyl)-1,3-thiazol-2-yl] hydrazinylidene}methyl]phenol (3b) 28 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a Tổng hợp 4-bromo-2-[{2-[4-(4-nitrophenyl)-1,3-thiazol-2-yl]hydrazin ylidene}methyl]phenol (3c) 29 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b Tổng hợp 4-bromo-2-[{2-[4-(3-nitrophenyl)-1,3-thiazol-2-yl] hydrazinylidene}methyl]phenol (3d) 29 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 Tổng hợp 3-{2-[-2-(5-bromo-2-hydroxybenzylidene)hydrazinyl]-1,3thiazol-4-yl}-2H-chromen-2-one (3e) .30 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b Tổng hợp 6-bromo-3-{2-[2-(5-bromo-2-hydroxybenzylidene)hydra zinyl]1,3-thiazol-4-yl}-2H-chromen-2-one (3f) 31 f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e III XÁC ĐỊNH NHIỆT ĐỘ NÓNG CHẢY VÀ PHỔ CỦA CÁC CHẤT 33 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e Nhiệt độ nóng chảy .33 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d Phổ hồng ngoại (IR) 33 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 Phổ cộng hưởng từ hạt nhân ( H-NMR) .33 CHƯƠNG III: KẾT QUẢ VÀ THẢO LUẬN .34 I TỔNG HỢP 5-BROMO-2HYDROXYBENZALDEHYDE (1) 35 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Cơ chế phản ứng 35 Phân tích phổ 35 II TỔNG HỢP 5-BROMO-2-HYDROXYBENZALDEHYDE THIOSEMICARBAZONE (2) .38 Cơ chế phản ứng 38 Phân tích phổ 39 III TỔNG HỢP CÁC HỢP CHẤT CHỨA DỊ VÒNG THIAZOLE (3) 40 Cơ chế phản ứng 41 Phân tích phổ 41 CHƯƠNG IV: KẾT LUẬN 53 PHỤ LỤC .60 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 LỜI MỞ ĐẦU Trong năm gần đây, hóa học hợp chất dị vòng phát triển cách mạnh mẽ Số lượng hợp chất dị vòng tổng hợp ngày nhiều, đặc tính tính chất chúng nghiên cứu ngày đầy đủ hệ thống Nhiều đặc tính quý báu hợp chất dị vòng khám phá ứng dụng vào lĩnh vực đời sống sản xuất ngày phong phú, đa dạng Các hợp chất dị vòng thơm oxazole, imidazole, thiazole… nhận nhiều quan tâm nghiên cứu nhà khoa học ứng dụng chúng ngành sản xuất như: hóa dược, phẩm nhuộm…ngồi cịn ứng dụng hợp chất có hoạt tính sinh học… Trong số dị vịng thiazole tỏ trung tâm mang dược tính đáng để quan tâm nghiên cứu Một số hợp chất chứa dị vòng thiazole dùng làm thuốc vitamin B (thiamine), Peniciline, Ritonavir Theo nghiên cứu nhiều tác giả dị vịng thiazole có khả chống nấm [12, 26], kháng viêm [3, 16, 25], chống co giật [19, 29], chống ung thư [10], gây ức chế phân chia tế bào [5] Với mong muốn tổng hợp chất chứa dị vịng thiazole đồng thời chứa nhóm khác nhằm góp phần vào việc nghiên cứu dị vịng thiazole Chúng định chọn đề tài: 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 “TỔNG HỢP MỘT SỐ HỢP CHẤT CHỨA DỊ VÒNG THIAZOLE TỪ 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc 5-BROMO-2-HYDROXYBEZALDEHYDE” c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 Chúng tơi thực hện đề tài nhằm mục đích: tổng hợp hợp chất fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b chứa dị vòng thiazole dẫn xuất 5-bomo-2-hydroxybenzaldehyde Cụ thể là: fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b Từ 2-hydroxybenzaldehyde thực phản ứng electrophile gắn nhóm f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 -Br vào vị trí số phân tử 2-hydroxybenzaldehyde tạo thành 5-bomo-2- 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b hydroxy benzaldehyde (1) 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 Sau cho (1) ngưng tụ với thiosemicarbazide (NH NHCSNH ) tạo 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 thành 5-bomo-2-hydroxybenzaldehyde thiosemicarbazone (2) 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Cuối thực phản ứng Hantzsch (2) với dẫn xuất α-bromoacetophenone dẫn xuất 3-(2-bromoacetyl)coumarin thu hợp chất chứa dị vòng thiazole (3a-f) Nghiên cứu tính chất vật lý chất tổng hợp cách xác định nhiệt độ nóng chảy, màu sắc, dung môi kết tinh… Xác định cấu trúc chất tổng hợp cách phân tích phổ hồng ngoại (IR), phổ cộng hưởng từ hạt nhân (1H-NMR) 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 CHƯƠNG I : TỔNG QUAN 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 I GIỚI THIỆU CHUNG VỀ DỊ VÒNG THIAZOLE Vài nét cấu tạo Thiazole hợp chất dị vòng cạnh thuộc họ 1,3-azole (imidazole, oxazole, thiazole) phân tử có nguyên tử nitơ nguyên tử lưu huỳnh chiếm vị trí 1,3 với Theo thuyết orbital phân tử (MO) dị vịng thiazole có cấu tạo phẳng, vịng có hệ thống electron π, bao gồm electron π liên kết C=C, electron π liên kết C=N cặp electron p nguyên tử lưu huỳnh Thỏa mãn quy tắc Huckel (4n+2) nên vòng thiazole có tính thơm Năng lượng liên hợp thơm vào khoảng 84 kJ/mol [1] Tính bền vững thiazole định có mặt hệ electron π giải tỏa toàn phân tử Ngoài ra, ngun tử nitơ cịn 1cặp electron khơng tham gia vào ổn định tính thơm vịng nên dị vòng thiazole 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e có tính base yếu e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a Theo quan điểm thuyết cộng hóa trị (VB) cấu trúc dị vịng thiazole xem lai hóa cộng hưởng dãy dạng cộng hưởng khác 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc [19] c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 N N N 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 N N 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b S S S S S f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 (II) (I) (III) (IV) (V) 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e Trong cấu (I) khơng mang điện tích đóng góp chính, cấu 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d cộng hưởng khác khơng bền, cấu trúc (II) bền cấu trúc cịn lại Điều giải thích mặt cấu tạo dị vịng thiazole tồn chủ yếu theo cấu trúc (I) Tính chất 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Thiazole chất lỏng màu vàng nhạt nhiệt độ sôi khoảng 116-118oC Thiazole tan nước, tan tốt rượu ether II PHƯƠNG PHÁP TỔNG HỢP MỘT SỐ HỢP CHẤT CHỨA DỊ VỊNG THIAZOLE Có nhiều phương pháp tổng hợp dị vịng thiazole dẫn xuất như: phương pháp Hantzsch, tổng hợp Garbriel, tổng hợp Kook-Heilbron, tổng hợp Tcherniac nhiều phương pháp khác… Tuy nhiên theo tài liệu cho thấy dị vòng thiazole tổng hợp chủ yếu theo hai phương pháp mà chúng tơi trình bày Phương pháp đóng vịng gián tiếp thông qua hợp chất α-halocarbonyl (phương pháp Hantzsch) Đây phương pháp tổng hợp dị vòng thiazole nghiên cứu, sử dụng rộng rãi phổ biến Theo phương pháp này, từ hợp chất α-halocarbonyl hợp chất mang nhóm -NHC(=S)- (thiourea, thioamide dẫn xuất [5]) Ví dụ thiazole (6) khơng có nhóm sinh ngưng tụ chloroacetaldehyde (4) với thioamide (5) Cl S H2C CH S to 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e HC e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 NH2 O N 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 (5) (4) (6) 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b Phản ứng đạt hiệu suất thấp thioamide khơng bền Tuy nhiên đồng đẳng thioamide bền vững nhiều, phản ứng điều kiện đơn 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 giản [1] 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 S Cl S CH3 H2C df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 N benzen O NH2 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 C C H3C CH3 95oC 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e H3C 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 (7) (8) (9) 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 Ứng dụng phương pháp này, nhiều tác giả tổng hợp số hợp chất chứa dị vòng thiazole sau: 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 13 10 12 11 NH N HO Br N 17 S Phụ lục 9: Phổ 1H-NMR đầy đủ 4-bromo-2-((2-(4-(4-bromophenyl)-1,3-thiazol-2-yl)hydrazinylidene) methyl) phenol (3b) 14 16 15 Br 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 10 N HO Br NH Phụ lục 10: Phổ 1H-NMR giãn rộng 4-bromo-2-((2-(4-(4-bromophenyl)-1,3-thiazol-2-yl)hydrazinylidene) methyl) phenol (3b) 14 11 S N 17 12 13 16 15 Br 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 13 10 12 11 N HO Br NH 17 S N Phụ lục 11: Phổ hồng ngoại 4-bromo-2-((2-(4-(4-nitrophenyl)-1,3-thiazol-2-yl) hydrazinylidene) methyl) phenol (3c) 14 16 15 O2N 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 13 10 12 11 NH N HO Br N 17 S Phụ lục 12: Phổ 1H-NMR đầy đủ 4-bromo-2-((2-(4-(4-nitrophenyl)-1,3-thiazol-2-yl) hydrazinylidene) methyl) phenol (3c) 14 16 15 O2N 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 13 10 12 11 HO Br NH N 17 S N Phụ lục 13: Phổ 1H-NMR giãn rộng 4-bromo-2-((2-(4-(4-nitrophenyl)-1,3-thiazol-2-yl) hydrazinylidene) methyl) phenol (3 ) 14 16 15 O2N 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 HO Br NH N Phụ lục 14: Phổ hồng ngoại 4-bromo-2-((2-(4-(3-nitrophenyl)-1,3-thiazol-2-yl) hydrazinylidene) methyl) phenol (3d) 10 11 S N 17 16 12 13 15 14 NO2 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 N HO Br NH Phụ lục 15: Phổ 1H-NMR đầy đủ 4-bromo-2-((2-(4-(3-nitrophenyl)-1,3-thiazol-2-yl) hydrazinylidene) methyl) phenol (3d) 10 11 S N 17 16 12 13 15 14 NO2 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Br HO Phụ lục 16: Phổ 1H-NMR giãn rộng 4-bromo-2-((2-(4-(3-nitrophenyl)-1,3-thiazol-2-yl) hydrazinylidene) methyl) phenol (3d) 10 11 NH N 17 S N 16 12 13 15 14 NO2 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 14 10 13 12 11 S NH N HO Br N O Phụ lục 17: Phổ hồng ngoại 3-(2-(-2-(5-bromo-2-hydroxybenzylidene)hydrazinyl)-1,3thiazol-4-yl)-2H-chromen-2-one (3e) 15 16 17 18 O 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 14 10 13 12 11 S NH N HO Br N O Phụ lục 18: Phổ 1H-NMR đầy đủ 3-(2-(-2-(5-bromo-2-hydroxybenzylidene)hydrazinyl)-1,3thiazol-4-yl) -2H-chromen-2-one (3e) 15 16 17 18 O 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 14 10 13 12 11 S NH N HO Br N O Phụ lục 19: Phổ 1H-NMR giãn rộng 3-(2-(-2-(5-bromo-2-hydroxybenzylidene)hydrazinyl)-1,3thiazol-4-yl) -2H-chromen-2-one (3e) 15 16 17 18 O 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 10 12 11 S NH N HO Br N O 13 O Phụ lục 20: Phổ hồng ngoại 6-bromo-3-(2-(2-(5-bromo-2-hydroxybenzylidene)hydrazinyl) thiazol-4-yl) -2H-chromen-2-one (3f) 15 16 14 18 17 Br 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 10 11 12 S NH N HO Br N O 13 O Phụ lục 21: Phổ 1H-NMR đầy đủ 6-bromo-3-(2-(2-(5-bromo-2-hydroxybenzylidene)hydrazinyl) thiazol-4-yl) -2H-chromen-2-one (3f) 16 15 14 18 17 Br 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 10 12 11 S NH N HO Br N O 13 O Phụ lục 22: Phổ 1H-NMR giãn rộng của6-bromo-3-(2-(2-(5-bromo-2-hydroxybenzylidene)hydrazinyl) thiazol-4-yl) Phụ lục 1: Phổ hồng ngoại 5-bromo-2-hydroxybenzaldehyede (1) -2H-chromen-2-one (3f) 15 16 14 18 17 Br 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 7d0800 c6a8 0136 f54 da448 1c2 b397 7f6 f33 e0be 8a4b3 d678 cc5b77 828 cc3 7ae38 f66a4 9c84a7 1dc1cb825a 4f1 d7c732fb9a4 e5765 f83 10c1984 f96 1e06 cf3 fc71f185b5ad74 b fac7b7b2 0dfcfdcdf1 cf4 2b2 fc6 b5a c1e9 c4a51ae fef5b7 de7f4b3 cc9e5d780d33d5 94 9e3f2 1bf4656 147e4 1c5 63d1 76a97 9e946 6be8 9c63 c0e 2907 0df0e654 8e28 c32 c6 f8f7 7ea8e433 c9 f051 8c9 06b9a 684d9d02 5cb598 854db148 3a8024 9bc348 7e1be 4646 2d7a b f21d145b5b08 b8e1 f8 c76 f42 b4ce 759fb93 c48 e7f8a41e7 8571e 64a2 f48b0e5 c8d4 bb8 df3 fa34df8 f2c9de ba5dcb1e e30bc7d67cb1d4163 72d9 47cdab0 1c5 76b2 b2efb3 c49a2 08d258 539 bc6 96d5a 3b1a4 c49 7180 bae30 dc4 4793a3 dc5d19 4ad09 3cb5c3f9 9f2 02398 30ff2d29 b07 f39 d69e d7d2 e358bfca d25b40c5434 0e68a b4ee2 b76e0 b2a8 65300 be6e 95f4 fcb5fd1f4 934 f29e7 ee6d7cfa 31ddc0 5b49 f94 3c1 e22 f3b5 c0e4a d46 2e7c96fc5b 3f9 f11 c9f0 8a6db91a1 7118e 3de6 3e7a02 f9 c1d19137 7d0a7a 34d40ff5b8 453 f6f4e0e 59e15a9 f853 8397 40b3 e9ac33e6fc51 7d8 b739 3a5076 c67 d16e 7cc03df1 b1f0b9 fc0 46 3a67e368 0a4d3d50 cf8d5 f476 8201 e328 cbbba50 c741 ebd4f6 b2e1 0316e d218 e1d2 918 0d4204 90efb3ab05fb73 c76 f04 f402 4609 30bbbd8c70 8725 e74dc8 cf9a 5b23 c6 ce52 6d 5a2ffad28c03f5ddc8 b5b1 9f6 5a9a4 f8ff22e 5e28b515a6 e2baff25 e0185 e7457 d94 b3 6e74e1a5 eb8e 6a6629 e94dc3 b8533 4599 8a334 c325 5d17 f25 1a9f0fc09d15d4 76fc381 14dd4 024 c2f27f32d2 1896e 863 d2798 93b4 5fb87d4d3 b709a d32bf1 f855 3822 14eb1 0a 4a2b893 e6f264e6 3adfe30c144aa d9ad6 d154a 23f6b2 be48 d55b74c3677 f31a2 6752 77 Ý KIẾN CỦA HỘI ĐỒNG CHỦ TỊCH HỘI ĐỒNG: ……………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… THƯ KÝ HỘI ĐỒNG: ………………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… …………………………………………………………………………………… 6f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 6e0cf7 b60da 52f6cf66 b5ff294 1e747 e e1b11a9 32da b860 f81 b6f9bdc32 ecac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f8 932dab860 f81b6f9 bdc32e cac7776e 0cf7b6 0da5 2f6 cf66b5ff2 941e 747e6 f87e 1b1 1a ỦY VIÊN HỘI ĐỒNG: ………… …………………………………………… 860f8 1b6 f9bdc32eca c77 76e0 cf7 b60 da52 f6cf66 b5ff29 41e74 7e6f87e1 b11a9 32da b f81b6f9 bdc32e cac7 776e0 cf7b6 0da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b86 6f9bdc3 2eca c77 76e0 cf7 b60 da52 f6cf66 b5ff294 1e74 7e6f87e1 b11a9 32dab860 f81 b …………………………………………………………………………………… dc32e cac7776 e0cf7b60da5 2f6 cf66b5ff2941e 747e 6f87 e1b1 1a932 dab8 60f81b6 f9 b 32eca c7776 e0cf7 b60da 52f6cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc …………………………………………………………………………………… c7776 e0cf7b60da 52f6 cf66b5ff2941 e747e 6f8 7e1b11a932 dab8 60f81b6 f9 bdc32e ca e0cf7b60 da52 f6 cf6 6b5ff2 941e7 47e6 f87e 1b11a 932da b860 f81 b6 f9bdc3 2eca c777 …………………………………………………………………………………… fc3a3 f93a 08582 6d66a 60f835 d2406 ea15 f7e7 b88cbf5e9cb78 cc9e16 d1072 e24 c3ee4 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