Chemistry of Heterocyclic Compounds. Volume 31. Chromenes, Chromanones, and Chromones

1198 Pages·1935·68.26 MB·english

by  Ellis G.P.

CHROMENES, CHROMANONES
AND CHROMONES
This is the Thirty-First Vohrme it! !he Series
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
~
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
A SERIES OF MONOGRAPHS
ARNOLD WEISSBERGER and EDWARD C. TAYLOR
Editors
C H R O M E N E S ,
C H R O M A N O N E S ,
A N D C H R O M O N E S
Edited by
G. Ellis
P.
UNIVERSITY OF WALES INSTITUTE OF SCIENCE AND TECHNOLOGY,
CARDIFF, UNITED KINGDOM
AN INTERSCIENCE @ PUBLICATION
JOHN WILEY & SONS
NEW YORK LONDON SYDNEY TORONTO
An Interscience @)Publication
Copyright @ 1977 by John Wiley & Sons, Inc.
All rights reserved. Published simultaneously in Canada.
No part of this book may be reproduced by any means,
nor transmitted, nor translated into a machine language
without the written permission of the publisher.
Library of Congress Cataloging in Publication Data:
Main entry under title:
Chromenes, chromanones, and chromones.
(The chemistry of heterocyclic compounds; 3 1)
“An Interscience publication.”
Includes bibliographical references and indexes.
1. Benzopyran. 2. Chroman. 3. Chromone.
I. Ellis, Gwynn Pennant.
QD405.C47 547l.592 76-57932
ISBN 0-471-38212-4
Authors
G. Ellis, Department of Chemistry, University of Wales Institute of Science
P.
and Technology, Cardiff
I. M. Lockhart, Prochem, BOC Limited, London
(Mrs.) Deborah Meeder-Nycz, Department of Chemistry, University of
Delaware, Newark, Delaware
E. E. Schweizer, Department of Chemistry, University of Delaware, Newark,
Delaware
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 subdivisions have been designed to
cover the field in its entirety by monographs which reflect the importance and
the interrelations of the various compounds, 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 progress. If,
however, the changes are not too great so that the first editions can be brought
up-to-date by supplementary volumes, supplements to the respective volumes
will be published in the first edition.
ARNOLDW EISSBERCER
Research Laboratories
Eastman Kodak Company
Rochester, New York
EDWARDC . TAYLOR
Princeton University
Princeton. New Jersey
The literature on benzopyrans requires several volumes for adequate coverage.
In this volume several arbitrary limitations had to be made so that a survey of
the chosen field could be completed in reasonable time. Consequently this book
is confined to chromenes, chromanones, chromones, and closely related com-
pounds (the precise scope of the book is given in Chapter I). Flavones, iso-
flavones, and coumarins, for example, are excluded because their extensive
literature justifies separate volumes. It is hoped that the writing of such books
will be a slightly less daunting task now that the simpler I-benzopyrans have
been reviewed.
I am grateful to my coauthors for their cooperation. The General Editors of
this series and the Publisher have been very helpful at all stages. In addition, I
wish to thank the following: those researchers who sent me reprints of their
own publications and exchanged views with me on points of interest; Mr. A. H.
Henson, who made useful comments on the chapters that he kindly read: and
my co-workers in this Department (some of whom were generously supported
by Messrs. Allen and Hanburys Limited), who helped to maintain my interest
in chromones. Much credit is due to Mrs. P. M. Bevan, who expertly typed
many of the chapters. I wish to thank owners of copyrighted material for
permission to include it in this book.
I am greatly indebted to my daughter, Rosalind, for much linguistic help
with papers in several foreign languages. Finally, without the patience and
assistance of my wife at all stages, writing and editing the book would have
been an impossible task. Apart from giving much active help, she and my
daughter tolerantly and understandingly accepted my reclusive habits while the
work was in progress.
G. P. ELLIS
CardiJJ Wales
November 1976
Contents
I. Chromenes, Chromanones, and Chromones-Introduction 1
G. P. ELLIS
11. 2H- and 4H- I-Benzopyrans 11
E. E. SCHWEIZER AND DEBORAH MEEDER-NYCZ
Ill. 3- and 4-Chromanols 14 1
I. M. LOCKHART
IV. 3-Chromanones 193
1. M. LOCKHART
V. 4-Chromanones 207
I. M. LOCKHART
VI. 2,4-C hromandiones and 2,3,4-Chromantriones 429
I. M. LOCKHART
VII. Naturally Occurring Chromones 455
G. P. ELLIS
VIII. Analytical Aspects of Chromones 48 1
G. P. ELLIS
IX. General Methods of Preparing Chromones 495
G. P. ELLIS
X. Chromone and Its Benzo Derivatives 557
G. P. ELLIS
XI. Alkylchromones 581
G. P. ELLIS
XII. Hydroxy chromones 633
G. P. ELLIS
XIII. Alkoxychromones 69 1
G. P. ELLIS
XIV. Halochromones 749
G. P. ELLIS
xii Contents
xv. Nitrochromones 78 1
G. P. ELLIS
XVI. Aminochromones 799
G. P. ELLIS
XVII. Ketonic Chromones 855
G. P. ELLIS
XVIII. Chromone Carbonitriles and Tetrazole Derivatives 90 3
G. P. ELLIS
XIX. C hromone Carboxaldehydes 92 1
G. P. ELLIS
xx. Chromone Carboxylic Acids and Their Derivatives 943
G. P. ELLIS
XXI. Bischromones and Bichromones 1043
G. P. ELLIS
Author Index 1085
Subject Index
CHROMENES, CHROMANONES
AND CHROMONES
This is rhe Thirry-First Voiitme it7 rhe Series
THE CHEMISTRY OF HETEROCYCLIC
COMPOUNDS