Free ebooks ==> www.Ebook777.com www.Ebook777.com Free ebooks ==> www.Ebook777.com www.Ebook777.com CHEMISTRY RESEARCH AND APPLICATIONS SERIES HETEROCYCLIC COMPOUNDS: SYNTHESIS, PROPERTIES AND APPLICATIONS No part of this digital document may be reproduced, stored in a retrieval system or transmitted in any form or by any means The publisher has taken reasonable care in the preparation of this digital document, but makes no expressed or implied warranty of any kind and assumes no responsibility for any errors or omissions No liability is assumed for incidental or consequential damages in connection with or arising out of information contained herein This digital document is sold with the clear understanding that the publisher is not engaged in rendering legal, medical or any other professional services CHEMISTRY RESEARCH AND APPLICATIONS SERIES Applied Electrochemistry Vijay G Singh (Editor) 2010 ISBN: 978-1-60876-208-8 Heterocyclic Compounds: Synthesis, Properties and Applications Kristian Nylund and Peder Johansson (Editors) 2010 ISBN: 978-1-60876-368-9 Free ebooks ==> www.Ebook777.com CHEMISTRY RESEARCH AND APPLICATIONS SERIES HETEROCYCLIC COMPOUNDS: SYNTHESIS, PROPERTIES AND APPLICATIONS KRISTIAN NYLUND AND PEDER JOHANSSON EDITORS Nova Science Publishers, Inc New York www.Ebook777.com Copyright © 2010 by Nova Science Publishers, Inc All rights reserved No part of this book may be reproduced, stored in a retrieval system or transmitted in any form or by any means: electronic, electrostatic, magnetic, tape, mechanical photocopying, recording or otherwise without the written permission of the Publisher For permission to use material from this book please contact us: Telephone 631-231-7269; Fax 631-231-8175 Web Site: http://www.novapublishers.com NOTICE TO THE READER The Publisher has taken reasonable care in the preparation of this book, but makes no expressed or implied warranty of any kind and assumes no responsibility for any errors or omissions No liability is assumed for incidental or consequential damages in connection with or arising out of information contained in this book The Publisher shall not be liable for any special, consequential, or exemplary damages resulting, in whole or in part, from the readers’ use of, or reliance upon, this material Independent verification should be sought for any data, advice or recommendations contained in this book In addition, no responsibility is assumed by the publisher for any injury and/or damage to persons or property arising from any methods, products, instructions, ideas or otherwise contained in this publication This publication is designed to provide accurate and authoritative information with regard to the subject matter covered herein It is sold with the clear understanding that the Publisher is not engaged in rendering legal or any other professional services If legal or any other expert assistance is required, the services of a competent person should be sought FROM A DECLARATION OF PARTICIPANTS JOINTLY ADOPTED BY A COMMITTEE OF THE AMERICAN BAR ASSOCIATION AND A COMMITTEE OF PUBLISHERS LIBRARY OF CONGRESS CATALOGING-IN-PUBLICATION DATA Library of Congress Cataloging-in-Publication Data Heterocyclic compounds : synthesis, properties, and applications / Kristian Nylund and Peder Johansson p cm Includes bibliographical references and index ISBN 978-1-61324-989-5 (eBook) Heterocyclic compounds I Nylund, Kristian, 1956- II Johansson, Peder, 1945QD400.H467 2009 547'.59 dc22 2009040473 York CONTENTS Preface Chapter Chapter vii Substituted 2-Aminothiophenes: Synthesis, Properties and Applications Z Puterová and A Krutošíková Adamantyl-1 and Adamantyl-2 Imidazoles and Benzimidazoles Methods of Synthesis, Properties and Biological Activity D S Zurabishvili, M O Lomidze, M V Trapaidze,Sh A Samsoniya Chapter Methods of Synthesis of Pyrroloindoles Sh A Samsoniya, I Sh Chikvaidze, D O Kadzhrishvili, N L Targamadze Chapter Palladium-catalyzed Amination of Dihaloarenes: A Simple and Efficient Approach to Polyazamacrocycles Alexei D Averin, Alexei N Uglov, Alla Lemeune, Roger Guilard, Irina P Beletskaya Chapter Pyrridazinoindoles, Synthesis and Properties Sh A Samsoniya, I Sh Chikvaidze, M Ozdesh 47 99 119 147 vi Chapter Chapter Chapter Chapter Chapter 10 Chapter 11 Chapter 12 Index Contents 11-Perfluoroalkyl-substituted 3,3-Dimethyl11-hydroxy-2,3,4,5,10,11-hexahydro-1Hdibenzo[b,e][1,4]diazepin-1-ones: Synthesis and Characterization Tatyana S Khlebnicova, Veronika G Isakova, Alexander V Baranovsky and Fedor A Lakhvich Synthesis and Biological Activity of some Isomeric Dipyrrolonaphthaline Derivatives Sh A Samsoniya, M V Trapaidze, N A Esakia, K.Kh.Mamulashvili, Z Sh Lomtatidze, T V Doroshenko 171 183 Some Conversions of 5-acetyl-2-ethoxycarbonyl - 3-p-nitrophenyl Indole N Narimanidze, Sh Samsoniya, I Chikvaidze 201 2-Pyridineselenenyl- and Tellurenyl Chlorides as Building Blocks for Derivatives of 2,3-dihydro[1,3] selen(tellur)azolo[3,2-a] pyridin-4-ium Alexander V Borisov, Zhanna V Matsulevich, Vladimir K Osmanov, Galina N Borisova and Georgy K Fukin 211 Synthesis and Antimicrobial Activity of some Adamantyl Containing Indoles and Benzopyrroloindole Derivatives Sh A Samsoniya, D S Zurabishvili, I Sh Chikvaidze, M O Lomidze, M V Trapaidze, K Kh Mamulashvili, Z Sh Lomtatidze 219 Photochemistry of Azidopyridine and Related Heterocyclic Azides Mikhayl F Budyka 225 Progress in the Chemistry of Condensed Thiazolopyrimidines M.A Metwally and Bakr F Abdel-Wahab 317 377 PREFACE Heterocyclic compounds are organic compounds containing at least one atom of carbon, and at least one element other than carbon, such as sulfur, oxygen or nitrogen within a ring structure These structures may comprise either simple aromatic rings or non-aromatic rings Some examples are pyridine (C5H5N), pyrimidine (C4H4N2) and dioxane (C4H8O2) Many heterocyclic compounds, including some amines, are carcinogenic This book details the proposed mechanisms of Gewald-like reactions and the wide scope of substituted 2aminothiophenes for real life applications Literary information about synthesis methods, structure, physical-chemical and biological properties is summarized, and also information about conversion of adamantyl-1 and adamantyl-2 imidazole and benzimidazole derivatives is given A survey of the literature of thiazolopyrimidines from 2003 to 2008; some of the commercial applications of thiazolopyrimidine derivatives are mentioned Chapter - Several methods are accessible for synthesis of substituted 2aminothiophenes: cyclization of thioamides and their S-alkylates, Schmidt reaction of 2-nitrothiophenes, Beckmann rearrangement of 2-acetylthiopheneoximes, anyway since 1961 when first report on the Gewald reaction was published it became an universal method for this purpose and has gained prominence in recent times The availability of the reagents and the mild reaction conditions all contribute to the versatility of this reaction The improved variations of the Gewald reaction offer several additional advantages such as tolerating a broad range of functional groups The mechanism of this powerful reaction is not fully clear Consequently, this chapter details about the proposed mechanisms of Gewald-like reactions and the wide scope of substituted 2-aminothiophenes for real life applications Free ebooks ==> www.Ebook777.com viii Kristian Nylund and Peder Johansson Title compounds are attractive derivatives, largely used in the industry because of their applications in pharmaceuticals, agriculture, pesticides and dispersed dyes They exhibit antimicrobiological activity against various Gram (+) and Gram (-) bacteria and fungi Many of these molecules act as allosteric enhancers of A1-adenosine receptor, glucagon antagonists as well as antioxidant and anti-inflammatory agents Moreover, they are potent precursors in synthesis oligo- and polythiophene structures, which are employed to create novel types of semi conducting polymers and non-linear optic materials Chapter - The interest towards adamantylcontaining imidazoles and benzimidazoles is stipulated by broad spectrum of their biological effects and important technical properties At present, different methods of synthesis are elaborated and definite success in study of the structure features and reactivity of imidazole and benzimidazole derivatives of adamantane series is achieved In this survey, literary information about synthesis methods, structure, physical-chemical and biological properties is summarized, and also information about conversion of adamantyl-1 and adamantyl-2 imidazole and benzimidazole derivatives is given The bibliography includes 96 references Chapter - Two alternative methods of synthesis of unsubstituted pyrroloindoles have been worked out by Professor Sh Samsoniya and his coworkers at Iv Javakhishvili Tbilisi State University According to the first method the attachment of pyrrole ring occurs to benzene ring of indoline; and pursuant to the second method two pyrrole rings are attached to benzene ring In the both methods for formation of pyrrole rings is used Fischer reaction In the first method the initial compounds are 5- and 6- aminoindolines Their diazotization and further reduction gives the corresponging hydrazines, by condensation of which with pyruvic acid ethyl ether are obtained corresponding hydrazones, which in polyphosphoric acid ethyl ether (ppaee) undergo cyclization to yield mixture of angular and linear pyrroloindoline ethers, with great excess of linear isomers By saponifying of ether with subsequent decarboxylation and simultaneous dehydration on pd/C are obtained fully aromatized, unsubstituted, isopmeric pyrroloindoles In the second method as initial compound is used m-phenylenediamine, by diazotization and subsequent reduction of which is obtained dihydrazine which condensate with pyruvic acid ethyl ether to yield the corresponding dihydrazone Its cyclization in ppaee results the built of two pyrrole rings on benzene ring The mixture of angular and linear pyrroloindole diethers is being formed, with great excess of angular isomers The subsequent saponifying and decarboxylation of diethers result the corresponding unsubstituted pyrroloindoles www.Ebook777.com ... Related Heterocyclic Azides Mikhayl F Budyka 225 Progress in the Chemistry of Condensed Thiazolopyrimidines M.A Metwally and Bakr F Abdel-Wahab 317 377 PREFACE Heterocyclic compounds are organic compounds. .. biologically important compounds The title compounds are subdivided into groups according to the position of fusion between thiazole and pyrimidine rings In: Heterocyclic Compounds: Synthesis,... obtain biologically active compounds The majority of obtained compounds have been tested on initial biological activity, such as bactericidal, tuberculostatic activities Three compounds have revealed