Chemistry of Heterocyclic Compounds: Synthesis of Fused Heterocycles: Part 2, Volume 47

776 Pages·1992·76.26 MB·English

OF FUSED HETEROCYCLES
SYNTHESIS
PART 2
This is (he .suc*otid purl of the Forry-siwrirlr Volunre in [hi. Serii.s
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
A SERIFS OF MONOGRAPHS
EDWARD C. TAYLOR
Editor
.. -- -. - -.. .. . .- .. . -. .. .. .. . - . - .. . .. . .. .... . . .. . .. .. . . - . . .. - . ,. -. - . ..
SYNTHESIS OF FUSED
HETEROCYCLES
PART 2
Copyright @ 1902 by John Wilcy & Sons Ltd.
Baftins Lime, Chichcsler,
Wcrt Sus*x IUD. England
PO19
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John Wilcy & Sons (SEA) PCI Lid. 37 Jaian Pcmimpin #OS-O4,
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Library a/ Congress Calal~gin~in-PublicD~ait~a n
(Revised lor volumc 2)
Ellis G. P. (Gwynn Pcnnant)
Synthesis of luwd hcicrwyclcs.
(The Chemistry ol hctcrcwyclic compounds:
v. 47)
'A Wilcy-intcrxicncc publication'.
Hibliogriphy: p. SXl-632: v. 1. p.
Includes indexes.
I. Heterocyclic chemistry. 2. Organic
compounds-Synthesis. 3. Hctcnryclic
compounds. I. Titlc.
QDM).WS 19x7 547'59 X6-2X944
ISBN 0471 913.11 2 (v. I)
ISBN 0 471 93070 (v. 2)
9
British Library Cataloguing in Publicatian Data
A cataloguc record lor this bc~kis available lrom thc British Library
ISBN 0 47 I 93070 9
Introduction to the Series
The series Thc Chcniistrj I$ Hetcvwylic Conipoicirc1.s. published since I950 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 synthesis, reactions. properties, structure, physical
chemistry and utility of compounds helonging 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 kcoinr
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 irnpinpc on almost all aspects of
modem organic and medicinal chemistry. For this reason we initiated several years
ago a parallel series entitled Giwrwl Hi~tiw~iyliCcl.r eniistry which treated such
topics as nuclear mangetic resonance of heterocyclic compounds. inass spectra
of heterocyclic compounds. photochemistry of hetensylic compounds. the utility
of heterocyclic compounds in organic synthesis and the synthesis d hetcrwyclic
compounds by means of 1 ,Mipolar cycloaddition rcactions. 'These volumes were
intended to be of interest to all organic chemists. its well its to those whose particular
concern is heterocyclic chemistry.
It became 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 Gcvic*sul Hi*two(.ylkC ircwris/i:v.a nd
to publish all fonhcoming volumes in the general area of heterocyclic chemistry
in Tile Circniisrsy of Ht~tc~ruw:wlCico nipoiiiidv series.
Eklward C. Taylor
Department of Chemistry
Princeton University
Princeton, New Jersey 08544
V
Contents
Preface xi
I. Introduction 66 I
2. Acetal or Aldehyde and Amine or Carboxamide 670
3. Acetal and Ring-carbon or Ring-nitrogen 67.5
4. Acylamine and Aldehyde or Ketone 680
5. Acylamine or Carbamate and Amiiie or Hydrazine 683
6. Acylamine and Carboxamidc 690
7. Acylamine and a Carboxylic Acid Derivative 693
8. Acylamine or Amine and Ether 607
9. Acylamine, Acylhydrazine. Amine or Isocyanate and Halogen 70 I
10. Acylamine or Amine and Hydroxy 712
I I. Acylamine or Diazonium Salt and Lactam Carbonyl 726
12. Acylamine or lmine and Methylene or Alkene 733
13. Acylamine or Amine and Nitrile 730
14. Acylamine. Amine or Imine and Nitro 7s 1
1.5. Acylamine or Amine and Nitroso or N-Oxide 756
16. Acylamine, Acyloxy, Amine or Hydroxy and Phosphorane 760
17. Acylamine or Acylhydrazine and Ring-carhon 767
18. Acylamine or Acylhydrazine and Ring-nitrogen 775
19. Acylamine or Amine and Sulphonamide or Thioureide 778
10. Acylamine or Amine and Thiwyanate 78 I
2 I. Acyl Halide and Ring-carbon or Ring-nitrogen 783
22. Aldehyde or Ketone and Alkene or Alkyne 786
23. Aldehyde or Ketone and Azide or Triazene 7w
24. Aldehyde or Ketone and Carbamate. Isothiocyanate or Thiourea 792
25. Aldehyde or Ketone and Carboxamide or Sulphonamide 794
26. Aldehyde or Ketone and Carboxylic Acid or Ester 799
27. Aldehyde or Ketone and Ether 806
28. Aldehyde or Ketone and Halogen 809
29. Aldehyde. Ketone or Lactam Carbonyl and Hydroxy x17
vii
viii Contents
30. Aldehyde and Ketone: Dialdehyde or Diketone 827
3 I. Aldehyde or Ketone and Methylene 839
32. Aldehyde or Ketone and Nitrile
M5
33. Aldehyde or Ketone and Nitro. Nitroso or N-Oxide 848
34. Aldehyde or Other Carbonyl and Phosphorane 852
Aldehyde or Ketone and Ring-carbon 859
35.
36. Aldehyde. Ketone or Lactam Carbonyl and Ring-nitrogen 872
37. Alkene or Alkyne and Amine, Azide or Nitro 884
38. Alkene or Alkyne and Carboxylic Acid or its Derivative 89 1
39. Alkene or Alkyne and Halogen 893
40. Alkene or Alkyne and Hydroxy or Erher 898
4 I. Alkene. Methylene or Ring-carbon and Lactam or Lactone Carbonyl 904
42. Alkene or Alkyne and Methylene. Ring-carbon or Ring-nitrogen 910
43. Amidine and Amine. Carboxylic Acid or its Derivative 92 1
44. Amidine and Ring-carbon or Ring-nitropen 927
45. Amine and Azide. Azo or Diazo 932
46. Amine or Phosphorane and Carboxamide 935
47. Amine and Carboxylic Acid 940
48. Amine and Carboxylic Ester 946
49. Amine and Enamine or Oxime 957
SO. Amine or Diazonium Salt and Hydrizide or Hydrazine 959
51. Amine and Hydrazone or Imine
964
52. Amine and Ketone 969
Amine and Ring-carbon 980
53.
54. Amine and Ring-nitrogen 997
55. Azide and Aro or Nitro 1015
56. Azide or Isocyanate and a Carboxylic Acid Derivative 1018
57. Azide or Am and Methyl or Methylene 1020
58. Azide or Azo and Ring-carbon 1023
59. Azide and Ring-nitrogen 1030
60. Azo and Carbamate 1033
6 I. Carbamate or Ureide and Ring-carbon or Ring-nitropen 1035
62. Carbamate or Carboxamide and another Carboxylic Acid Derivative 1040
63. Carboxamide or Nitrile and Diazonium Salt 1045
64. Carboxamide. Nitrile or Ureide and Hydroxy or Ether 1047
65. Carboxamide or Nitrile and Ring-carbon or Ring-nitrogen 1054
66. Carboxylic Acid or its Derivative and Halogen 1063
67. Carbox& Acid or Ester and Hydrazine ocHydroxylamine Derivative 1073
68. Carboxylic Acid. Acyl Chloride or Ester and Hydroxy or Ether 1076
69. Carboxylic Acid Derivative and Lactam Carbonyl, Cyanate or
Isocyanate 108 I
70. Carboxylic Acid Derivative, Lactam Carbonyl or Isocyanide and
Methylene I086
Contents ix
7 I. Carboxylic Acid Halide or Ester and Nitrile 1094
72. Carboxylic Acid. its derivative or Lactarn Cirbnyl and Nitro or
Ureide 1096
73. Carboxylic Acid or Ester and Ring-carbon 1 105
74. Carboxylic Acid or Ester and Ring-nitrogen 1112
75. Carboxylic Acid or its Derivative and a Sulphur-containing Group 1118
76. I ,2-Diarnine 1123
77. 1 5 . 1.4- or 1.5-Diarnine 1142
78. Diazo or DiaLonium Salt and Halogen or Methylene 1 I47
79. Diazo or Diazoniurn Sdr and Ring-carbon or Ring-nitrogen I IS0
isx
80. Dicarboxylic Acid or its Derivative or Diazide I
8 I. Dihalogen 1163
82. Dihydroxy 1170
83. Dinitriie or Dinitro I I77
84. Di-ring-carbon or Di-ringnitrogen 11x1
85. Enarnine and Ester or Ketone 120u
86. Enarnine and a Non-carbonyl Group 1204
87. Ether and Methylene, Ring-carbon or Ring-nitrogen I'O X
88. Halogen and Ether or Hydroxy 1213
89. Halogen and Lactarn Carbonyl or a Sulphur-containing Group 1219
Halogen and Merhylene or Ring-carbon 1222
90.
91. Halogen and Nitro 1233
92. Halogen and Ring-nitrogen 1236
93. Hydrdzide, Hydrdzine or Hydrazone and Nitro 1244
94. Hydrazine and Ring-carbon or Ring-nitrogen 1247
95. Hydrazone or Oxirne and Ring-carbon or Ring-nitrogen 1260
96. Hydroxy or Ether and Hydrazone or Oxime 1267
97. Hydroxy and Methylene 1272
98. Hydroxy and Nitro or Ring-nitrogen 1276
99. Hydroxy and Ring-carbon 1280
100. Hydroxy, Ring-carbon or Ring-nitrogen and lrnine or
Irn inophosphorine 1293
101, Isocyanate and Methylene. Ring-catbon or Ring-nitrogen 1303
102. Ketone and Lactarn Carbonyl 1307
103. Methylene and Nitro or Nitroso 1.312
104. Methylene and Ring-carbon or Ring-nitrogen 1316
10s. Nitro or N-Oxide and Ring-carbon or Ring-nitrogen 132x
106. Ring-carbon or Ring-sulphur and Ring-Nitrogen 1335
List of Books and Monographs 1343
References 1345
General Index 1399
Index of Ring Systems 141I
Preface
The warm reception given to Sy~rrlri~soisj' Frrsetl tlc~ri~lncybl~y sr eviewers and
readers since its puhlication in I087 has encouraged me to prepare another classified
selection of methods by which a new hetercryclic ring may be built on to a
(cartxxyclic or heterocyclic) ring. The I987 ht~di(w hich was reprinted with minor
corrections in 1991 ) is referred to in this book as S~1rr1rcsi.rs! f'Fir.s~~lcir/ ri~rv~c;\.r.lc.s.
Pwr 1. The layout of the present volume is siiililar to that of Part I but some
improvements have ken ninde. These are described in the last two parilgraphs of
Chapter I. Section II. Part 1 contains over two tliousand references (including those
nunikred iIS 3037a. 3027b. 3059a. 30.5% 2067:~3 067b. etc.) not listed in Part I.
I wish to thank reviewers and readers who 1iiiIdt useful suggestions following
the puhlicatioii of Part I: tor example. Professor Brilntlsniit suggested in a review
of Part I that. in a product containing two or more heterocyclic rings. the index
should show the newly toniied ring in hold letter\. The Index of Ring Systcms ;it
the end of this volume follows this suggestion.
I dso thank Mr A. J. Cannard BSc for writing ;I computer progrimi which
overcomes the problem of idphabetiAtig the n;uiics of those fused heterocycles
which begin with numbers iind/or contain locants which need to be pilflially ignored
during the production of an index which is useful to organic chemists. Thanks are
also due to the staff of thc lihraries of the University of Wdes colleges iit Cardiff
and Bangor.
I wish to thank my wife for enduring long pcricds of isolation while this book
was king written. iind for her advice i111d help when needed. Professor E. C.
Taylor and thc staff of John Wiley & Sons itt Chichcster have constantly provided
encouragement and help for which I ilnl griiteful.
xi
Chemistry of Heterocyclic Compounds, Volume4 7
G. P. Ellis
Copyright 0 1992 by John Wiley & Sons, Ltd.
CHAPTER I*
Introduction
1. Aims 661
11. scope 662
111. Use of the 664
Book
I. One- and Two-step Reactions 664
2. Naming of Functional Groups 665
3. Approved Names and Formulae 666
4. Format 668
IV. Abbreviations 669
1. AIMS
This is intended to provide a convenient way of locating papers (and
book
reviews) on methods for the synthesis of a heterocyclic ring which is fused to
another ring. Figure 1 .I shows diagrammatically the types of cyclizations
covered. The z-ring may be either homocyclic or heterocyclic. and may be of any
size; the newly formed P-ring is heterocyclic and contains five to eight atoms, at
least one of which (Z) is nitrogen, oxygen or sulphur. Atoms A and B may or
may not be identical and may be carbon or nitrogen (or rarely sulphur, in which
*This is a modified and expanded version of Chapter I. Part I
66 I