InterBioScreen Monograph Series

SELECTED METHODS
FOR SYNTHESIS AND MODIFICATION
OF HETEROCYCLES

Edited by Prof. V.G. Kartsev

International Editorial Board:
Prof. Corey E.J. (USA, Nobel Prize in Chemistry 1990),
Prof. Noyori R. (Japan, Nobel Prize in Chemistry 2001),
Prof. Huisgen R. (Germany),
Prof. Van der Plas H.C. (The Netherlands),
Prof. Katritzky A.R. (USA).

1 Volume, 576 pages, Moscow: IBS Press, 2002
2 Volume, 536 pages, Moscow: IBS Press, 2003

 


ATTENTION !

 This CD edition for the FIRST TIME makes it possible to work in ISIS.2 - search format by both textual (author/s, paper title) and structural fragments. Included DB contains 603 information units describing over 2,800 chemical formulae and over 1500 reactions.

Volume 1 opens up a series of monographs on the chemistry of heterocyclic compounds based on the newest data obtained at the universities and research institutes in Russia, Ukraine, Belarus, and other republics of the Commonwealth of Independent States and Baltic states of the former Soviet Union that are now separated by frontiers but united by many years of close cooperation and common background.

The book (vol. 1) is a collection of invited reviews (and selected synthetic procedures) on some aspects of synthesis, characterization, and properties of nitrogen-containing heterocycles and their biological activity.

I am grateful to all of the contributors for concise presentation of their new and intriguing results, techniques, and well-documented review papers.

It is planned that the oncoming vol. 2 be devoted to the synthetic chemistry of oxygen- and sulfur-containing heterocycles. Still further volumes will be devoted to the chemistry and biological activity of various naturally occurring compounds and their synthetic derivatives.

I would like to express my hope that this series will draw attention of the worldwide chemical community which will also contribute to our forthcoming publications.

We are quite aware that the book may have numerous deficiencies. Many hard decisions had to be made of what to put in and what to leave out, so that we have probably overlooked some important contributions. Despite our best efforts, undoubtedly some errors remain, for which we take full responsibility.

The idea of publishing this series and financial support came from InterBioScreen Russian company, one of worldwide leaders in targeted synthesis of new organic compounds and modification of natural compounds in cooperation with pharmaceutical, agrochemical, biotech companies and universities all around the world.

I hope that the data presented in this book will be interesting and instructive to a wide audience: researchers in the field of organic synthesis and chemical engineering (both at universities and industrial companies), medicinal and pharmaceutical chemistry, food chemistry, chemistry of natural compounds, agriculture, veterinary science, graduate and postgraduate students, etc.


Prof. Dr. Victor G. Kartsev
CEO InterBioScreen
Moscow, December 2002

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INTERBIOSCREEN MONOGRAPH SERIES



SELECTED METHODS
FOR SYNTHESIS
AND MODIFICATION
OF HETEROCYCLES


Edited by Prof. V.G. Kartsev

Volume 1

INTERBIOSCREEN MONOGRAPH SERIES



SELECTED METHODS
FOR SYNTHESIS
AND MODIFICATION
OF HETEROCYCLES


Edited by Prof. V.G. Kartsev

Volume 2
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CONTENTS
VOLUME 1

Akhrem A.A., Gulyakevich O.V., Mikhal'chuk A.L.
[3+3]-Cyclocondensation of cyclic Schiff bases in synthesis of annelated quinolizine derivatives
7
Demchenko A.M., Lozinskii M.O.
Heterocyclic N-arylamidines: Synthesis and properties
27
Desenko S.M., Chebanov V.A., Kolos N.N., Orlov V.D.
Cyclocondensation of aromatic and heteroaromatic 1,2-diamines with a, b-unsaturated carbonyls
48
Dyachenko V.D., Roman S.V.
Naphthyridines: Chemistry and biological activity
74
Egorova A.Yu., Timofeeva Z.Yu.
Synthesis of pyrrol-2-ones
87
Glushkov V.A.
3-Benzazepines
107
Golikov A.G., Kriven'ko A.P., Reshetov P.V.
Stereodirected synthesis of fused N-hydroxyalkyl piperidines
127
Grandberg I.I.
Synthesis of indolylalkylamines and related compounds from g-, d-halocarbonyls and arylhydrazines
140
Granik V.G., Ryabova S.Yu., Golovko T.V.
Heterocyclization of indoxyl and oxindole derivatives
151
Ivanov E.I.
The chemistry of cyclohomologs of xanthine
175
Klochkova I.N., Semenova N.N.
Perhydroazoles and perhydroazines: Synthesis and applications
188
Kochergin P.M., Druzhinina A.A.
Derivatives of pyrrole-containing heteroaromatics with a bridgehead nitrogen atom: Synthesis according to Chichibabin
206

Korotkikh N.I., Rayenko G.F., Kiselyov A.V., Knishevitsky A.V., Shvaika O.P., Cowley A.H., Jones J.N., Macdonald C.L.B.
Synthesis of stable heteroaromatic carbenes of the benzimidazole and 1,2,4-triazole series and their precursors
220
Kovtunenko V.A., Kisil' V.M.
Annelated quinazolines
241
Kozminykh V.O., Kozminykh E.N.
Acylpyruvic acids in synthesis of N-heterocycles
263
Krasnov K.A.
Barbituric acids in synthesis of new heterocycles: 1. Synthesis of azaheterocycles
280
Mikhalenok S.G., Kuz'menok N.M., Zvonok A.M.
Alkaloids of the pyrrolo[1,2-b]pyrazole series: Synthesis of withasomnine and its analogs
312
Mikhaleva A.I., Schmidt E.Yu.
Two-step synthesis of pyrroles from ketones and acetylenes through the Trofimov reaction
334
Serov A.B., Kartsev V.G., Aleksandrov Yu.A.
Ylides of nitrogeneous bases in reactions of 1,3-dipolar cycloaddition
353
Shikhaliev Kh.S., Falaleev A.V., Kryl'skii D.V.
Guanidines in synthesis of azaheterocycles
377
Shklyaev Yu.V.
Synthesis of 3,3-dialkyl-3,4-dihydroisoquinoline derivatives
404
Shklyaev Yu.V., Glushkov V.A.
1-Substituted 3,3-dialkyl-3,4-dihydroisoquinolines as nucleo- and electrophilic reagents
417
Tolstikov G.A., Dembitskii V.M., Tolstikova T.G., Shults E.E.
Epibatidine and the problem of non-opioid analgesics
438
Best synthetic methods
469-568
Author index
569-571

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Volume 2 is devoted to the chemistry of O- and S-containing heterocyclic compounds, including the N-containing ones. This is the 2-nd volume in the IBS series of monographs Selected Methods for Synthesis and Modification of Heterocycles (vol. 1 devoted to N-containing heterocycles appeared in early 2003 at IBS Press, Moscow). The book covers a wide range of heterocyclic compounds-from oxiranes and thiiranes to complex naturally occurring and synthetic condensed systems. Much attention is given to the biological activity of these compounds and other aspects of their practical implementation, which makes the book interesting not only to synthetic chemists but also to biochemists, pharmacologists, and medicinal chemists. The most of these reviews will make a basis for the plenary lectures to be presented at the II International Conference on the Chemistry and Biological Activity of O- and S-Containing Heterocycles (Moscow, October 14-17, 2003) that continues the series of international meetings on the Chemistry and Biological Activity of Synthetic and Natural Compounds sponsored and organized by Scientific Partnership Foundation and InterBioScreen Ltd. under the aegis of the Russian Academy of Sciences and National Academies of Sciences from the Baltic and CIS countries.

Of especial pride for us is the kind consent of outstanding and renowned chemists-Prof. E. Corey (Nobel Prize, 1990), Harvard University, USA; Prof. R. Noyori (Nobel Prize, 2001), Nagoya University, Japan; Prof. À. Katritzky, University of Florida, USA; Prof. R. Huisgen, University of Munchen, Germany; Prof. H.C. van der Plas, University of Wageningen, Netherlands; and Prof. J. Bergman, Novum Unit of Organic Chemistry, CNT, Sweden-to participate, as honorary members, in the work our Editorial Board.

This imposes a still higher responsibility on us as concerning proper selection of submitted papers for publication and as regarding the technical quality of the book. We hope that our monographs (including this volume) will be interesting and instructive to a wide circle of readers-to the researchers active in the fields of organic synthesis, medicinal chemistry, chemistry of natural compounds, as well as to respective graduate and postgraduate students.


V.G. Kartsev
Moscow, April 2003


CONTENTS
VOLUME 2
Adekenov S.M., Kulyyasov A.T.
Synthesis of sesquiterpenoids substituted in the lactone ring
7
Belen'kii L.I.
Preparative chemistry of stable 2H-thiophenium ions
24
Dyachenko V.D., Tkachev R.P.
Activated alkoxyethylenes in synthesis of bioactive pyridine and quinoline derivatives
33
Erzhanov K.B., Kurmankulov N.B., Batyrbekova A.B.
Cyclization of propargyl compounds
53
Fazylov S.D., Gazaliev A.M., Nurkenov O.A.
Heterocyclic derivatives of ephedrine alkaloids
63
Gornostaev L.M., Lavrikova T.I., Arnold E.V., Podvyazny O.V.
Functionalization of anthra- and naphthoquinones
72
Grandberg I.I., Nam N.L.
Condensed systems based on amino- and oxypyrazoles
83
Ishchenko V.V., Khilya V.P.
Synthesis of 2-hetarylchromones
95
Kartsev V.G., Lakeev S.N., Maidanova I.O., Galin F.Z., Tolstikov G.A.
Sulfur ylides in synthesis of heterocyclic compounds
107
Khilya V.P., Ishchenko V.V.
Synthesis of 3-aryl and 3-hetarylchromones
140
Khilya V.P., Shablykina O.V., Ishchenko V.V.
Synthesis of hetarylcoumarins
154
Kozminykh V.O., Kozminykh E.N.
Acylpyruvic acids in synthesis of O- and N-containing heterocycles
169
Krasnov K.A.
Barbituric acids in synthesis of new heterocyclic systems.
2. Synthesis of pyrimidine derivatives annelated with O- and S-containing heterocycles
183
Levkovskaya G.G., Bozhenkov G.V., Mirskova A.N.
Synthesis of heterocycles from chloro- and bromovinyl ketones
207
Lozinskii M.O., Demchenko A.M., Shivanyuk A.F.
Synthesis and properties of 1,4-benzothiazines
228
Lozinskii M.O., Shelyakin V.V.
Cyclocondensation of heterocyclic 1,3-dicarbonyls and their derivatives in synthesis of O-, N-, and S-containing heterocycles
257
Maslivets A.N., Lisovenko N.Yu.
4,5-Disubstituted 2,3-dihydrofuran-2,3-diones: Synthesis and chemical behavior
282
Nekrasov D.D.
Synthesis and chemical behavior of oxazolidine-4,5-diones
316
Rodinovskaya L.A., Chunikhin K.S., Shestopalov A.M.
a-Nitrocarbonyls, their derivatives, and a,b-unsaturated nitro compounds in synthesis of heterocycles
325
Ryndina S.A., Êàdushkin À.V., Granik V.G.
Pyrimidine cyclization based on 3-amino derivatives of thiophene and pyrrole
356
Shestopalov A.M., Emel'yanova Yu.M.
Synthesis and biological activity of substituted 2-amino-4H-pyrans
363
Tolkunov S.V.
Benzothieno[2,3-c]pyridines and benzofuro[2,3-c]pyridines: Synthesis, properties, and biological activity
391
Ukhin L.Yu.
Nitrogenous derivatives of aromatic aldehydes and enamines in synthesis of heterocyclic compounds
411
Velikorodov A.V.
Carbamates and their polyfunctional derivatives in synthesis of azaheterocycles
438
Vizer S.A.
Formation of heterocycles upon catalytic carbonylation of acetylenic compounds
464

Vizer S.A., Erzhanov K.B.
Synthesis of heterocycles by catalytic intramolecular cyclization of acetylenic compounds

475

Zhuravel' I.A., Karasev À.À., Kovalenko S.N., Chernykh V.P.
Chemistry of azacoumarins

503

Author index

534-535
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