Organic Chemistry of Drug Synthesis, Vol. 2.pdf

anic Chemistry
of Drug Synthesis
VOLUME 2
DANIEL LEDNICER
Mead Johnson pany
Evansville, Indiana
LESTER A. MITSCHER
The University of Kansas School of Pharmacy
Department of Medicinal Chemistry
Lawrence, Kansas
A WILEY-INTERSCIENCE PUBLICATION
JOHN WILEY AND SONS, New York • Chichester • Brisbane • Toronto
Copyright © 1980 by John Wiley & Sons, Inc.
All rights reserved. Published simultaneously in Canada.
Reproduction or translation of any part of this work
beyond that permitted by 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 & Sons, Inc.
Library of Congress Cataloging in Publication Data:
Lednicer, Daniel, 1929-
anic chemistry of drug synthesis.
"A Wiley-lnterscience publication."
1. Chemistry, Medical and pharmaceutical.
2. Drugs. 3. Chemistry, Organic. I. Mitscher,
Lester A., joint author. II. Title.
RS421 .L423 615M 91 76-28387
ISBN 0-471-04392-3
Printed in the United States of America
10 987654321
It is our pleasure again to dedicate
a book to our helpmeets: Beryle and Betty.
"Has it ever occurred to you that medicinal chemists
are just pulsive gamblers: the pound
will be the real winner."
R. L. Clark at the 16th National
Medicinal Chemistry Symposium,
June, 1978.
vii
Preface
The reception accorded "Organic Chemistry of Drug
Synthesis11 seems to us to indicate widespread interest
in anic chemistry involved in the search for
new pharmaceutical agents. We are only too aware of
the fact that the book deals with a limited segment
of the field; the earlier volume cannot be considered
prehensive pletely up to date.
Because the earlier book did, however, lay the
groundwork for many of the structural classes or
pounds that have proven useful in the
clinic, it forms a natural base for a series that
will, in fact, prehe