Heterocyclic Compounds: Synthesis, Properties and Applications

403 Pages·2010·3.25 MB·English

by  Kristian Nylund

CHEMISTRY RESEARCH AND APPLICATIONS SERIES

H C :
ETEROCYCLIC OMPOUNDS
S , P
YNTHESIS ROPERTIES
AND APPLICATIONS

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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
CHEMISTRY RESEARCH AND APPLICATIONS SERIES

H C :
ETEROCYCLIC OMPOUNDS
S , P
YNTHESIS ROPERTIES
AND APPLICATIONS

KRISTIAN NYLUND
AND
PEDER JOHANSSON
EDITORS

Nova Science Publishers, Inc.
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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)
1. Heterocyclic compounds. I. Nylund, Kristian, 1956- II. Johansson, Peder, 1945-
QD400.H467 2009
547'.59--dc22
2009040473

 York
CONTENTS

Preface vii
Chapter 1 Substituted 2-Aminothiophenes: Synthesis,
Properties and Applications 1
Z. Puterová and A. Krutošíková
Chapter 2 Adamantyl-1 and Adamantyl-2 Imidazoles and
Benzimidazoles. Methods of Synthesis,
Properties and Biological Activity 47
D. S. Zurabishvili, M. O. Lomidze,
M. V. Trapaidze,Sh. A. Samsoniya
Chapter 3 Methods of Synthesis of Pyrroloindoles 99
Sh. A. Samsoniya, I. Sh. Chikvaidze,
D. O. Kadzhrishvili, N. L. Targamadze
Chapter 4 Palladium-catalyzed Amination of Dihaloarenes:
A Simple and Efficient Approach to
Polyazamacrocycles 119
Alexei D. Averin, Alexei N. Uglov, Alla Lemeune,
Roger Guilard, Irina P. Beletskaya
Chapter 5 Pyrridazinoindoles, Synthesis and Properties 147
Sh. A. Samsoniya, I. Sh. Chikvaidze, M. Ozdesh
vi Contents
Chapter 6 11-Perfluoroalkyl-substituted 3,3-Dimethyl-
11-hydroxy-2,3,4,5,10,11-hexahydro-1H-
dibenzo[b,e][1,4]diazepin-1-ones: Synthesis
and Characterization 171
Tatyana S. Khlebnicova, Veronika G. Isakova,
Alexander V. Baranovsky and Fedor A. Lakhvich
Chapter 7 Synthesis and Biological Activity of some
Isomeric Dipyrrolonaphthaline Derivatives 183
Sh. A. Samsoniya, M. V. Trapaidze, N. A. Esakia,
K.Kh.Mamulashvili, Z. Sh. Lomtatidze,
T. V. Doroshenko
Chapter 8 Some Conversions of 5-acetyl-2-ethoxycarbonyl
- 3-p-nitrophenyl Indole 201
N. Narimanidze, Sh. Samsoniya, I. Chikvaidze
Chapter 9 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 211
Alexander V. Borisov, Zhanna V. Matsulevich,

Vladimir K. Osmanov, Galina N. Borisova
and Georgy K. Fukin
Chapter 10 Synthesis and Antimicrobial Activity of some
Adamantyl Containing Indoles and
Benzopyrroloindole Derivatives 219
Sh. A. Samsoniya, D. S. Zurabishvili,
I. Sh. Chikvaidze, M. O. Lomidze, M. V. Trapaidze,
K. Kh. Mamulashvili, Z. Sh. Lomtatidze
Chapter 11 Photochemistry of Azidopyridine and Related
Heterocyclic Azides 225
Mikhayl F. Budyka
Chapter 12 Progress in the Chemistry of Condensed
Thiazolopyrimidines 317
M.A. Metwally and Bakr F. Abdel-Wahab
Index 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 2-
aminothiophenes 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 1 - Several methods are accessible for synthesis of substituted 2-
aminothiophenes: cyclization of thioamides and their S-alkylates, Schmidt
reaction of 2-nitrothiophenes, Beckmann rearrangement of 2-acetylthiophene-
oximes, 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.
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 A -adenosine receptor, glucagon antagonists as well as antioxidant
1
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 2 - 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 3 - Two alternative methods of synthesis of unsubstituted
pyrroloindoles have been worked out by Professor Sh. Samsoniya and his co-
workers 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.