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Name Reactions in
Heterocyclic Chemistry II
Wiley Series on Comprehensive Name Reactions
Jie Jack Li,
Series Editor
Name Reactions in Heterocyclic Chemistry
Edited by Jie Jack Li
Name Reactions of Functional Group Transformations
Edited by Jie Jack Li
Name Reactions for Homologation, Part 1 and Part 2
Edited by Jie Jack Li
Name Reactions for Carbocyclic Ring Formations
Edited by Jie Jack Li
Name Reactions in Heterocyclic Chemistry II
Edited by Jie Jack Li
Name Reactions in
Heterocyclic Chemistry II
Edited by
Jie Jack Li
Bristol-Myers Squibb Company
Foreword by
E. J. Corey
Harvard University
©WILEY
A JOHN WILEY & SONS, INC., PUBLICATION
Copyright ¨ 2011 by John Wiley & Sons, Inc. All rights reserved
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Library of Congress Cataloging-in-Publication Data:
Name reactions in heterocyclic chemistry / edited by Jie Jack Li.
p. cm.
Includes bibliographical references and index.
ISBN 978-0-470-08508-0
1. Heterocyclic chemistry. 2. Chemical reactions. I. Li, Jie Jack.
QD400.N34 2005
547'
Printed in Singapore.
oBook ISBN: 978-1 -118-09282-8
ePDF ISBN: 978-1-118-09285-9
ePub ISBN: 978-1-118-09284-2
10 987654321
V
Contents
Foreword
viii
Preface
ix
Contributing Authors
xi
PART 1
THREE- AND FOUR-MEMBERED
HETEROCYCLES
1
Chapter 1
Aziridines and Epoxides
1
2
11
21
1.1
1.2
1.3
Blum Aziridine Synthesis
Gabriel-Heine Aziridine Isomerization
Shi Epoxidation
PART 2
FIVE-MEMBERED HETEROCYCLES
41
Chapter 2
Pyrroles and Pyrrolidines
41
42
53
60
72
2.1
2.2
2.3
2.4
Clauson-Kass Pyrrole Synthesis
Houben-Hoesch Acylation of Pyrroles
Overman Pyrrolidine Synthesis
Trofimov Synthesis of Pyrroles
Chapter 3 Indoles
3.1
3.2
3.3
3.4
3.5
3.6
3.7
3.8
3.9
3.10
3.11
3.12
83
84
91
102
112
125
133
143
167
175
187
197
207
Bischler-Mïhlau Indole Synthesis
Borsche-Drechsel Cyclization
Buchwald-Hartwig Indole Synthesis
Cadogan-Sundberg Indole Synthesis
Fukuyama Indole Synthesis
Gassman Oxindole Synthesis
Larock Indole Synthesis
Matinet Dioxindole Reaction
Mori-Ban Indole Synthesis
Sandmeyer Isatin Synthesis
Sommelet-Hauser Rearrangement
Stollç Oxindole Synthesis
Chapter 4 Furans and Oxazoles
4.1
4.2
4.3
4.4
4.5
213
214
221
225
233
242
Nierenstein Reaction
Davidson Oxazole Synthesis
Fischer Oxazole Synthesis
Japp Oxazole Synthesis
Schóllkopf Oxazole Synthesis
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