Nghiên cứu tổng hợp dẫn xuất quinoline isoquinoline và khảo sát hoạt tính sinh học

H CHÍ MINH ISOQUINOLINE - 2014 ISOQUINOLINE CHUYÊN NGÀNH: CÔNG N PGS.TS - 2014 T BÁCH KHOA : PGS.TS Bùi Th B u Huê HCM TS 2: n - Chuyên ngành I - : - ISOQUINOLINE VÀ II III N - isoquinoline : 21/01/2013 IV : V PGS.TS Bùi Th B u Huê 22/11/2013 TS - PGS.TS - - Cá - - T Khoa Khoa h Bách Khoa Tp T 3- -pyridine nhóm ethyl ester Z)-2-methyl-3-(pyridin-4- Z)- E) H-NMR, 13C-NMR, DEPT, COSY, HMBC, HSQC ABSTRACT A two steps synthesis methodology (Stobbe condensation then cyclization) was successfully used to prepare quinoline structure starting from 3-pyridine carbaldehyde However, when 4-pyridinecarbaldehyde was used, through Stobbe condensation - cyclization sequence, then reduction of ethyl ester to alcohol and oxidation of alcohol to aldehyde, (Z)-2-methyl-3-(pyridin-4-yl)propenal was obtained with a yield of 25.12% after all This result shows that the presence of nitrogen atom in pyridine ring may influence to the stereoselectivity of Stobbe condensation: (Z)-olefine isomer was obtained instead of (E) isomer This lead to the unsuccessful cyclization to form the isoquinoline but the decarboxylation was observed Structure of compounds were identified based on analysis of modern spectroscopy data including 1H-NMR, 13C-NMR, DEPT, COSY, HMBC, HSQC Keywords: quinoline, isoquinoline, Stobbe condensation, decarboxylation tháng 14 i 1.1.1 Quinoline 1.1.3.1 1.1.3.2 Doebner-Miller 1.1.3.3 p Combes 1.1.3.4 1.1.3.5 1.2 Iso isoquinoline 1.2.1 Isoquinoline 12 Bischler-Napieralski 12 Pictet-Gams 12 1.2.3 Pictet-Spengler 13 Pomeranz-Fritsch 13 1.2.3 1.3 13 14 ii 17 17 khóa 19 21 21 21 21 23 24 24 24 24 -hydroxyquinoline-6-carboxylate 25 25 (E)-3-(ethoxycarbonyl)-4-(pyridin-3-yl)but-3-enoic acid (2a) 25 -hydroxyquinoline-6-carboxylate (3a) 26 -hydroxyisoquinoline-6-carboxylate 27 Z)-3-(ethoxycarbonyl)-4-(pyridin-4-yl)but-3-enoic acid (2b) 27 Z)-ethyl 2-methyl-3-(pyridin-4-yl)prop-2-enoate (3b) 27 Z)-2-methyl-3-(pyridin-4-yl)prop-2-en-1-ol (4b) 28 3.3.4 Z)-2-methyl-3-(pyridin-4-yl)propenal (5b) 28 29 ... 4.2 -hydroxyisoquinoline-6-carboxylate 48 -hydroxyisoquinoline-6-carboxylate 48 (E)-3-(ethoxycarbonyl)-4-(pyridin-4-yl)but-3-enoic acid (2b) 49 iv -hydroxyisoquinoline-6-carboxylate... - Chuyên ngành I - : - ISOQUINOLINE VÀ II III N - isoquinoline : 21/01/2013 IV : V PGS.TS Bùi Th B u Huê 22/11/2013... Doebner-Miller 1.1.3.3 p Combes 1.1.3.4 1.1.3.5 1.2 Iso isoquinoline 1.2.1 Isoquinoline 12 Bischler-Napieralski 12 Pictet-Gams