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SYNTHESIS OF FUSED HETEROCYCLES

G. P. ELLIS

Department of Applied Chemistry University of Wales Institute of Science and Technology

Cardiff, Wales, U K

A Wiley-Interscience Publication

JOHN WILEY & SONS Chichester . New York . Brisbane . Toronto . Singapore

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THE CHEMIS'RY OF HETEROCYCLIC COMPOUNDS A SERIES OF MONOGRAPHS

EDWARD C. TAYLOR Editor


This i s rlw Forrj.-.seretifh Volume in rhe Srries

THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS


G. P. ELLIS

Department of Applied Chemistry University of Wales Institute of Science and Technology

Cardiff, Wales, U K

A Wiley-Interscience Publication

JOHN WILEY & SONS Chichester . New York . Brisbane . Toronto . Singapore

Copyright 0 1987 by John Wiley & Sons Ltd.

All rights reserved.

No part of this book may be reproduced by any means, or transmitted. or translated into a machine language without the written permission of the publisher.

Library of Congress Cataloging-in-Publication Data:

Ellis, G. P. (Gwynn Pennant) Synthesis of fused heterocycles.

(General heterocyclic chemistry series) ‘A Wiley-Interscience publication.’ Includes index. 1. Heterocyclic chemistry. 2. Chemistry,

Organic-Synthesis. 3. Heterocyclic compounds. I. Title. II. Series. QD400,E45 1987 547l.59 86-28944

ISBN 0-17 1-91 43 1-2 ISBN 13: 078-0-17 1-9 143 1-0

British Library Cataloguing in Publication Data:

Ellis, C . P. Synthesis of fused heterocycles.- (General heterocyclic chemistry series,

I . Chemistry, Organic-Synthesis 2. Heterocyclic compounds I. Title 11. Series 547.59 QD400.3

ISSN 0363-8626)

Introduction to the Series

The series The Chemistry of Heterocyclic Compounds, published since 1950 under the initial editorship of Arnold Weissberger, and later, until Dr. Weissberger’s death in 1984, under our joint editorship, was organized according to compound classes. Each volume dealt with syntheses, reactions, properties, structure, physical chemistry, and utility of compounds belonging to a specific ring system or class (e.g. pyridines, thiophenes, pyrimidines, three-membered ring systems). This series, which has attempted to make the extraordinarily complex and diverse field of heterocyclic chemistry as readily accessible and organized as possible, has become the basic reference collection for information on heterocyclic compounds.

However, many broader aspects of heterocyclic chemistry are now recognized as disciplines of general significance which impinge on almost all aspects of modern organic and medicinal chemistry. For this reason we initiated several years ago a parallel series entitled General Heterocyclic Chemistry which treated such topics as nuclear mangetic resonance of heterocyclic compounds, mass spectra of heterocyclic compounds, photochemistry of heterocyclic compounds, the utility of heterocyclic compounds in organic synthesis, and the synthesis of heterocyclic compounds by means of 1,3-dipolar cycloaddition reactions. These volumes were intended to be of interest to all organic chemists, as well as to those whose particular concern is heterocyclic chemistry.

It has become increasingly clear that this rather arbitrary distinction between the two series creates more problems than it solves. We have therefore elected to discontinue the more recently initiated series General Heterocyclic Chemistry, and to publish all forthcoming volumes in the general area of heterocyclic chemistry in The Chemistry of Heterocyclic Compounds series.

Edward C. Taylor

Department of Chemistry Princeton University Princeton, New Jersey 08544

V

Contents

Preface xi

1. 2. 3. 4. 5. 6. 7. 8. 9.

10. 11. 12. 13. 14. 15. 16. 17. 18. 19. 20. 21. 22. 23. 24. 25. 26. 27. 28. 29. 30.

Introduction Acetal or Aldehyde and Amine Acetal and Ring-carbon or Ring-nitrogen Acylamine and Aldehyde or Ketone Acylamine and Amine Acylamine or Carbamate and Carboxamide or Nitrile Acylamine and Carboxylic Acid or Ester Acylamine or Amine and Ether or Thioether Acylamine, Acylhydrazine or Amine and Halogen Acylamine or Amine and Hydroxy or Thiol Acylamine, Amine or Diazonium Salt and Lactam Carbonyl Acylamine or Amine and Methylene Acylamine or Amine and Nitrile Acylamine, Acylhydrazine, Amine or Carbamate and Nitro Acylamine or Amine and Nitroso or N-oxide Acylamine, Acyloxy, Amine or Hydroxy and Phosphorane Acylamine or Acylhydrazine and Ring-carbon or Ring-sulphur Acylamine or Acylhydrazine and Ring-nitrogen Acylamine or Amine and Sulphonamide, Thioureide or Ureide Acylamine or Amine and Thiocyanate . Acyl halide and Ring-carbon or Ring-nitrogen Aldehyde or Ketone and Alkene or Alkyne Aldehyde or Ketone and Azide Aldehyde or Ketone and Carbamate Aldehyde or Ketone and Carboxamide or Hydrazide Aldehyde or Ketone and Carboxylic Acid or Ester Aldehyde or Ketone and Ether or Thioether Aldehyde or Ketone and Halogen Aldehyde and Hydroxy, Thiol or Thiocyanate Aldehyde and Ketone; Dialdehyde or Diketone

vii

1 8

17 21 24 29 32 37 40 48 60 68 74 83 86 89 92 98

102 105 107 110 113 116 118 120 125 130 137 143

... VI11

31. 32. 33. 34. 35. 36. 3 7. 38. 39. 40. 41.

42. 43.

44. 45. 46. 47. 48. 49. 50. 51. 52. 53. 54. 55. 56. 57. 58. 59. 60. 61. 62. 63. 64.

65. 66. 67. 68. 69.

70. 71.

Con1

Aldehyde or Ketone and Methylene Aldehyde or Ketone and Nitrile Aldehyde or Ketone and Nitro, Nitroso or N-Oxide Aldehyde or other Carbonyl and Phosphorane Aldehyde or Ketone and Ring-carbon Aldehyde or Ketone and Ring-nitrogen Alkene or Alkyne and Arnine or Nitro Alkene or Alkyne and Carboxylic Acid or its Derivative Alkene or Alkyne and Halogen Alkene or Alkyne and Hydroxy, Thiol or Ethqr Alkene, Methylene, Ring-carbon, or Ring-nitrogen and Lactam Carbonyl Alkene or Alkyne and Methylene, Ring-carbon or Ring-nitrogen Arnidine and Arnine, Carboxylic Acid, Ester, Hydroxy, Methylene or Nitro Arnidine and Ring-carbon or Ring-nitrogen Arnine and Azo or Diazo Arnine and Carboxarnide or Thiocarboxarnide Arnine and Carboxylic Acid Arnine and Carboxylic Ester Arnine and Enarnine Amine and Hydrazide or Hydrazine Amine and Hydrazone or Irnine Amine and Ketone Amine and Ring-carbon or Ring-sulphur Amine and Ring-nitrogen Azide and Azo or Nitro h i d e and a Carboxylic Acid or its Derivative Azide and Methyl, Methylene or Methine Azide and Ring-carbon Azide and Ring-nitrogen Azo or Triazene and Carbarnate, Carboxylic Acid. Ester or Nitrile Carbarnate or Ureide and Ring-carbon or Ringnitrogen Carboxarnide and another Carboxylic Acid Derivative Carboxarnide or Sulphonamide and Diazonium Salt or Diazo Carboxamide, Hydroxamic Acid, Hydrazide, Nitrile or Ureide and Hydroxy or Ether Carboxarnide or Nitrile and Ring-carbon or Ring-nitrogen Carboxylic Acid or its Derivative and Halogen Carboxylic Acid or Ester and Hydrazide or Hydrazine Carboxylic Acid, Acyl Chloride or Ester and Hydroxy or Ether Carboxylic Acid or its Derivative and Lactam Carbonyl or Isocyanate Carboxylic Acid, Ester, Nitrile or Isonitrile and Methylene Carboxylic Acid Halide or Ester and Nitrile

Lents

154 157 159 161 166 175 180 184 187 189

193 197

203 206 208 210 219 226 239 24 1 246 25 1 262 276 292 294 297 299 304 307 309 317 320

322 328 336 347 3 50

357 362 3 70

Contents

72.

73. 74. 75.

76. 77. 78. 79. 80.

81. 82. 83. 84. 85. 86. 87. 88. 89. 90. 91. 92. 93. 94. 95. 96. 97. 98. 99.

loo. 101.

102. 103. 104. 105. 106. 107.

Carboxylic Acid, its Derivative or Lactam Carbonyl and Nitro or Ureide Carboxylic Acid or Ester and Ring-carbon Carboxylic Acid or Ester and Ring-nitrogen Carboxylic Acid or its Derivative and a Sulphinic or Sulphonic Acid Derivative 1.2-Diamine 1,3-, 1,4- and I , 5-Diamine Diazo or Diazonium Salt and Methylene Diazo or Diazonium Salt and Ring-carbon or Ring-nitrogen Dicarboxylic Acid, its Anhydride, Diacyl Halide, Diester or Di h ydrazide Dihalogen Diol or Dithiol Dinit rile Di-Ring-carbon or Di-Ring-nitrogen Enamine and Ester or Ketone Enamine and a Non-carbonyl Group Ether or Thioether and Ring-carbon or Ring-nitrogen Halogen and Hydroxy or Thiol Halogen and Lactam Carbonyl or a Sulphur-containing Group Halogen and Methylene or Ring-carbon Halogen and Nitro Halogen and Ring-nitrogen Hydrazide or Hydrazine and Nitro or Ring-nitrogen Hydrazine and Ring-carbon or Ring-nitrogen Hydrazone or Oxime and Ring-carbon or Ring-nitrogen Hydroxy and Ketone or Lactam Carbonyl Hydroxy and Methylene Hydroxy and Nitro. Nitroso or Ring-nitrogen Hydroxy or Thiol and Ring-carbon Imine and Hydroxy, Ring-carbon or Ring-nitrogen Isocyanate or Isothiocyanate and Methylene, Ring-carbon or Ring- nitrogen Ketone and Lactam Carbonyl Methylene and Nitro or Nitroso Methylene and Ring-carbon or Ring-nitrogen Nitro or N-oxide and Ring-carbon or Ring-nitrogen Ring-carbon and Ring-nitrogen Ring-nitrogen and Thiol or Lactam Thiocarbonyl

Appendix: Notes on Naming Some Fused Heterocycles List of Books and Monographs References General Index Index of Ring Systems

ix

373 378 387

394 398 426 433 436

442 446 45 1 456 458 464 469 47 3 477 48 5 489 492 497 503 508 522 528 533 537 540 547

550 554 558 562 568 57 I 573

578 581 583 633 639

Preface

Over the last couple of decades, there has been a remarkable expansion in heterocyclic chemistry. This has been accompanied by the publication of new journals and books in the field. Abstracting journals efficiently alert the reader about new syntheses and reactions, but the retrieval of methods of forming a new heterocyclic ring fused to a carbocyclic or heterocyclic ring is difficult. In our own research programmes, we felt the need for such cyclizations to be classified according to the functional groups present in the precursor. We were unable to find any source of such information, and this book was developed from a collection of such references.

It is not possible in one volume to include examples of all types of ring closures, and I apologize to any reader who fails to find his favourite cyclization. Most of the two thousand or so references cited were published since about 1970 and each of these provides further references to earlier work. This enables a collection of relevant references to be obtained with minimum of time and effort. Few if any books are entirely free of errors, and I shall appreciate being informed of any that have escaped my notice.

Without the help of a large computer and a well-written program, I doubt whether it would have been possible to complete the work of writing this book. I am therefore greatly indebted to my colleague Dr. Peter M. May (now of Murdoch University, Australia) who wrote the complex program and patiently showed me how to use it. I am grateful also to Dr. Gillian L. Christie and Mrs. A. E. Bisgood who gave me valuable computing assistance towards the end of the task; Dr.Kevin M. Quinlan too gave valuable help with the program. I would like to thank Professor Hans Suschitzky for advice and encouragement and Professor Edward C. Taylor for a continuing dialogue and for advice. Dr. R. W. White of Chemical Abstracts Service kindly enlightened me on some of the finer points of nomenclature.

My interest in heterocyclization was stimulated over several years by my research colleagues. I am grateful to Dr. T. M. Romney-Alexander for his willing help over a few weeks during which he acted as honorary postdoctoral assistant! I thank the staff of John Wiley for their encouragement and assistance at every stage.

xi

xii Preface

I owe many thanks to Mrs. P. M. Bevan, who patiently transformed the text of my manuscript into a typescript which was a delight to publisher and printer. Finally, I thank my wife for surviving many hours of isolation while the book was being written-we met only at meal times! As always, she provided invaluable and willing help as literary adviser and proof reader.

October 1986 G. P. Ellis

CHAPTER 1

Introduction I. Aims

11. scope 111. Use of the Book

1. One- and Two-step Reactions 2. Naming of Functional Groups 3. Approved Names and Formulae 4. Format

IV. Abbreviations

1. AIMS

This book is intended to provide a convenient way of locating papers (and reviews) on methods for the synthesis of a heterocyclic ring which is fused to another ring. Figure 1.1 shows diagrammatically the types of cyclizations covered. The a-ring may be either homocyclic or heterocyclic and be of any size; the newly formed fl-ring is heterocyclic and contains five to eight atoms at least one of which is nitrogen, oxygen or sulphur (Z). Atoms A and B may or may not be identical and may be carbon or nitrogen (or rarely, sulphur in which case it would not have a substituent, X or Y, attached to it). X and Y are usually functional groups but one of them may be hydrogen. It is rare for both to be hydrogen. When A is a double-bonded or pyridine-type nitrogen, then X is not present or is an N-oxide function.

The book is divided into chapters according to the identities of X and Y, the arrangement being alphabetical as far as possible. For example, reactants in which X and Y are amine and carboxamide, respectively, are considered in Chapter 46 while those where X and Y are hydroxy and methylene are contained in Chapter 99. Where only a few examples of a particular X and Y corpbination were found in the literature, these are integrated with closely related groups, for

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