Chemistry of Heterocyclic Compounds: Triazoles 1,2,4, Volume 37

800 Pages·1981·36.078 MB·English

TRlA ZOLES
124
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
A SERIFS OF MONOCvRAPHS
ARNOLD WEISSBERGER and EDWARD C. TAYLOR
Edflor\
TRIAZOLES
Carroll Temple, Jr.
SOCrmF.RN RFSEARCH INSTTTUTE
BIRMINGHAM. ALABAMA
Edited by
John A. Montgomery
-
__I__
AN IN ILKS< Ith( I- (@ PUB1 I< A I IOY
JOHN WlLEY & SONS
. . .
NEW YORK CHICHESTER BRISBANE TORONTO
____ __ - ___
ll_l_
An Interscience @ Publication
Copyright @ 1981 John Wiley & Inc.
by Sons,
All rights reserved. Published simultaneously in Canada.
Reproduction or translation of any part of this work
beyond that permitted hy Sections 107 or 108 of the
1976 United States Copyright Act without the permission
of the copyright owner is unlawful. Requests for
permission or further information should be addressed to
the Permissions Department. John Wiley B; Sons. Inc.
Library Congress Cataloging in Publication Data:
of
Tcmple, Carroll.
Triazoles I .'.A.
(The Chemistry of heterocyclic compounds: v. 37
ISSN OOh'J-3 154)
Includes indexes.
I. Triazoles. 1. Montgomery. John A. 11. Title.
OD30 1 .?7 547'3V.3 80- 15637
ISBN (1-47 I -04hCh-0
The Chemistry of Heterocyclic Compounds
The chemistry of heterocyclic compounds is one of the most complex
branches of organic chemistry. It is equally interesting for its theoretical
implications, for the diversity of its synthetic procedures, and for the
physiological and industrial significance of heterocyclic compounds.
A field of such importance and intrinsic difficulty should be made as
readily accessible as possible. and the lack of a modern detailed and
comprehensive presentation of heterocyclic chemistry is therefore keenly
felt. It is the intention of the present series to fill this gap by expert
presentations of the various branches of heterocyclic chemistry. The subdivi-
sions have been designed to cover the field in its entirety by monographs
which reflect the importance and the interrelations of the various com-
pounds, and accommodate the specific interests of the authors.
In order to continue to make heterocyclic chemistry as readily accessible
as possible new editions are planned for those areas where the respective
volumes in the first edition have become obsolete by overwhelming pro-
gress. If, however, the changes are not too great so that the first editions can
he brought up-to-date by supplementary volumes, supplements to the
respective volumes will be published in the first edition.
ARNOLD WEISSBERGER
Research Lahoraiories
Easttnan Kodak (.'ortipany
Rochester. New York
EDWARCD. T AYIX)R
Princeion Utiiversity
Princeion. Mew Jersey
V
Note to the Reader
The text and tables of this volume on 1,2,1-triazoles. triazolines, and
triazolidines have been comprehensively compiled through the use of Clteni -
ical Abstracts. The text was composed from abstracts and references present
in volumes S 1-85 (1957-1976) of Chemical Absrracfs. which covers the
period from the reviews of K. T. Potts (1961) and J. H. Boyer (I9 6 1). The
tables list the compounds indexed by Chertiical Abstracts for the period of
time from the Second Supplement of Beilstein (1929) through 1975 and also
the majority of compounds for 1976. Because of the large number of
compounds. only a small number of 1.2,3-triazoles. triazolines. and
triazolidines are listed individually in the Subject Index, which, however.
will refer to the text for a particular group of compounds. Also a particular
group of compounds can be located readily by inspection of the Contents.
For convenience in cross-checking. the sections of the text and the tables are
denoted by the same title and number. The arrangement of the sections of
text and tables has been classified according to the nature of the atom
connecting the substituent to the ring. which follows the order of carbon
(alkyl, aryl, carboxylic acid. acyl). nitrogen (amino. nitro. etc.). oxygen
azo,
(alkoxy, aroxy. etc.). sulfur (alkyl- and aryl- thio, sulfinyl. etc.). and halogen.
Those compounds that contain more than one representative function are
discussed and assembled. respectively. in the appropriate sections and
tablcs. In the text. references are indicated by ardbic numbers. which refer
to Chemical Abstracts numbers listed at the end of each section. Also, the
reference for a compound listed in the tables is denoted by a Cheriiical
Abstracts number. The latter, listed numerically in the master reference
section. will identify either the patent or journal reference. Prior to volume
66 ( 1067). Chetnical Abstracts denoted the position of compounds within an
abstract by a page number and a letter. either one or both of which might
not correspond exactly to the Chemic-al Abstracts number that identifies the
journal reference. For patents or journals that might not be readily availa-
ble. Chemical Abstracts can be consulted. In the text. footnotes are used for
those journal references that appeared prior. to Chemical Abstracts.
Compounds described by the title of the table are listed as parent. N-
alkoxy-, N-hydroxy-. N-. P-. and S-oxides. and organometallic radicals
substituted on either carbon or nitrogen are not considered a representative
function. and these compounds are listed with the parent triazole. All
compounds are listed alphabetically. When isomeric compounds are listed,
the isomer with the lowest number appears first. The tables containing the
alkyl or aryl compouiids include the substituted alkyl or aryl derivatives; for
example. triazole-3-acetic acid is listed under alkyl rather than carboxylic
acid derivatives. Also. the tables containing the amino compounds include
v11
...
Vlll Kote to the Reader
alkyl- or arylamino. acylamino. and hydrazino type compounds. The names
of compounds that are derivatives of another class have been changed and
listed in the tables as triazoles. For example. triazolylpyridine has been
listed as pyridyltriazole; (triazolyl)-2-propanone as acetonyltriazole. Further.
the names of imides and derivatives of guanazine have been changed. when
possible, and listed as the corresponding aminotriazoles. In contrast. hyd-
roxytriazoles. triazolol, and triazolones are listed as triazolinones; mercap-
totriazoles. triazolethiol. and triazolethione as triazolinethiones. Similar
considerations as described above apply to the triazolines and triazolidines.
Compounds containing conjunctive names are listed alphabetically. For
compounds with conjunctive names of mixed function. the chief function is
determined by the grouping.
CARROLTLE.M PLE.
JH.
Birrtiirtgkant. Alaburtia
Jurle 19x0
Acknowledgments
For his help and encouragement in the preparation of this book, I am
indebted to Dr. John A. Montgomery. Many other colleagues at Southern
Research Institute have also contributed their time to this work for which I
am very grateful. In addition, my thanks go to a large group of typists for
carrying out the arduous task of preparing the typescript, to the library staff
for providing most of the material from which the references and tables are
composed. to Chemical Abstracts Service for the availability of a rctrospec-
tive substructure search on triazoles for Volumes 68-83 of Chemical Ab-
stracts, and to Southern Research Institute for allowing the use of their
facilities.
C. T.
ix
Contents
INTRODUCTION
1
1 ALKYL- OR ARYL-MONOSUBSTITUTED 1,2,4TRI-
AZOLES
3
1. I 1 -Alkyl- or Aryl-Substituted 1H- 1,2.4-Triazoles 3
1.2 3-Alkyl- or Aryl-Substituted s-Triazoles 6
1.3 4-Alkyl- or Aryl-Substituted 4H- 1,2,4-Triazoles 10
2 ALKYL- OR ARYLDISUBSTITUTED 1,2,4-"RIAZOLES
30
2.1 1,3-Alkyl- or Aryl-Disubstituted 1H -1,2,4-Triazoles 31
2.2 1,s-Alkyl- or Aryl-Disubstituted 1 H- 1,2,4-Triazoles 33
2.3 3.4-Alkyl- or Aryl-Disubstituted 4H- 1,2,4-Triazoles 34
2.4 3.5-Alkyl- or Aryl-Disubstituted s-Triazoles 38
3 ALKYL- OR ARYL-TRISUBSTITUTED 1,2,4-TRIAZOLES 62
3. I 1.3.5-Alkyl- or Aryl-Trisubstituted 1H - 1.2,4-Triazoles 63
3.2 3,4,S-Alkyl- or Aryl-Trisubstituted 4H- I ,2,4-Triazoles 69
4 ACIDS AND THEIR
1,2,4-TRIAZOLECARBOXYLlC
FUNCTIONAL DERIVATIVES
96
5 ACY L- 1,2,4-TRIAZOLES 121
6 AMINO-1,2,4-TRIAZOLES
130
6.1a 3(or 130
5)-Amino(unsubstituted)-s-Triazoles
6.1b 3(or 135
5)-Amino(substituted)-s-Triazoles
6.2 3(or 5)-Amino- 1 H- 1,2,4-Triazoles 144
6.3 3(or 5bAmino-JH- 1.2,4-Tria~oles 151
6.3 4-Amino-JIj- 1.2.4-Triazoles 155
\i
xii cont ents
7 DIAMINO- AND 205
TRIAMINO-1,2,4-TRIAZOLES
7.1 3,s-Diamino- 1,2,4-Triazoles 205
7.2 Other Diamino- and Triamino- 1.2,4-Triazoles 211
8 AZIDO-, AZO-, DIAZO-, DIAZOAMINO (TRIAZENO-)-,
NITRAMINO-, NITROSAMINO-, AND NITRO-1,2,4-
TRIAZOLES CONTAINING ONE OR MORE OF THESE
FUNCTIONAL GROUPS 225
9 0-SUBSTITUTED OXY-l,2,4-TRIAZOLES 239
9.1 Alkyl-, Aryl- and Acyl- Mono- and Di-O-Substituted 1,2,3-
Triazoles 239
9.2 0-(1 ,2,4-Triazole) Derivatives of Phosphorous Acids 24 1
10 SSUBSTITUTED THIO-, SULFINYL-, OR SULFONYL-
1,2,4-TRIAZOLES,
3,3'-DITHOBIS[l,2,4-TRIAZOLES],
AND 1,2,4-TRIAZOLESULFONIC ACIDS AND THEIR
FUNnIONAL DERIVATIVES 251
10.1 Mono- and Di-S-Substituted Thio- 1.2.4-Triazoles 2s 1
10.2 3.3'-Dithiobis[ 1.2.4-triazolesI. Sulfinyl- or Sulfonyl-
l,2,3-
triazoles, and 1.2.3-Tria/olesulfonic Acids and Their Func-
tional Derivatives 258
10.2a 3,3'-Dit hiobis[ 1,2.4-triazoles] 258
10.2b S-Substituted Sulfinyl- or 259
Sulfonyl-l,2,4-Triazoles
10.2~ 1,2,4-Triazolesulfonic Acids and Their Functional Deriva-
tives 26 1
11 MONO-, D1-, AND TRIHALO-1,2,4-TRIAZOLES 288
12 1,2,4-TRIAZOLES CONTAINING MORE THAN ONE REP-
RESENTATIVE FUNCTION 297
12.1 Mono- and Diamino- Acids and
1,2,4-Triazolecarboxylic
Their Functional Derivatives 297
12.2 S-Substituted Thio-, Sulfinyl-, Sulfonyl-, and Acylthio- 1,2.4-
Triazolecarboxylic Acids and Their Functional Derivatives 30 1
12.3 Miscellaneous Acids and Their
1,2.4-Triazolecarboxylic
Functional Derivatives 302
12.4 Miscellaneous Acyl- 1.2,4-Triazoles 307
12.5 Amino-SSubstituted Thio-, Sulfinyl- or Sulfonyl-1 ,2,4-
Triazoles 31 1