Chemistry of Heterocyclic Compounds. Volume 38. Isoquinolines. Part II

547 Pages·22.59 MB·english

by  Kathawala F.G.

lSoQUINOLINEs
PART TWO
This is the rhirty-eighth wlumr in the series
THE CHEMISTRY HETEROCYCLIC COMPOUNDS
OF
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
c
A SERIES OF MONOGRAPHS
EDWARD C. TAYLOR, Editor
ARNOLD WEISSBERGER, Founding Editor
ISOQUINOLINES.
PART TWO
Edited by
F. G. Kathawala
Gary M. Coppola
Herbert F. Schuster
SANDOZ RESEARCH iNSTlTUTE
EAST HANOVER. NEW JERSEY
AN INTERSCIENCE @ PUBLICATION
JOHN WILEY & SONS
NEW YORK CHICHESTER BRISBANE TORONTO SINGAPORE
An Interscience @ Publication
Copyright 0 1990 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 I08 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.
Lihsry'ol C mCstsl oging in PVMiatioa Dsm
Main entry under title:
Isoquinoiines
(The Chemistry of Heterocyclic compounds ISSN 0069-3154)
"An Interscience-publication."
Includes index.
ISBN 0-471 -62856-5
I09 8 7 65 4 3 2 I
To my brother Rick
-G.M.C.
To Didi, Oliver, and Rene
-F.G.K.
To my wge, Maro
my daughter, Kristiana
my son, Stefan
-H.F.S.
The Chemistry of Heterocyclic
Compounds
Introduction to the Series
The chemistry of heterocyclic compounds constitutes one of the broadest and
most complex branches of chemistry. The diversity of synthetic methods utilized
in this field, coupled with the immense physiological and industrial significance
of heterocycles, combine to make the general heterocyclic arena of central
importance to organic chemistry.
The Chemistry of Heterocyclic Compounds. published since 1950 under the
initial editorship of Arnold Weissberger, and later, until Dr. Weissberger’s death
in 1984, under our joint editorship, has attempted to make the extra-
ordinarily complex and diverse field of heterocyclic chemistry as organized and
readily accessible as possible. Each volume has dealt with syntheses, reactions,
properties, structure, physical chemistry and utility of compounds belonging to a
specific ring system or class (e.g., pyridines, thiophenes, pyrimidines, three-
membered ring systems). This series has become the basic reference collection for
information on heterocyclic compounds.
Many broader aspects of heterocyclic chemistry are recognized as disciplines
of general significance which impinge on almost all aspects of modern organic
and medicinal chemistry, and for this reason we initiated several years ago a
parallel series entitled General Heterocyclic Chemistry, which treated such topics
as nuclear magnetic resonance, mass spectra, and photochemistry of heterocyclic
compounds, the utility of heterocyclic compounds in organic synthesis, and the
synthesis of heterocyclic compounds by means of 1,3-dipolar cycloaddition
reactions. These volumes were intended to of interest to all organic and
be
medicinal chemists, as well as to those whose particular concern is heterocyclic
chemistry.
It has become increasingly clear that this arbitrary distinction creates many
as
problems as it solves, and we have therefore elected to discontinue the more
recently initiated series General Heterocyclic Chemistry, and to publish all
forthcoming volumes in the general area of heterocyclic chemistry in The
Chemistry of Heterocyclic Compounds series.
EDWARCD. TAYLOR
Department of Chemistry
Princeton University
Princeton New Jersey
ix
Preface
A large number of alkaloids and other natural products carry the isoquinoline
skeleton. These natural products provide the basis for many intensive efforts
towards the development of new and useful therapeutic agents. As indicated in
the preface of Isoquinolines: Part One the purpose of the books on isoquinolines
is dual: an introduction for the beginner interested in the general chemistry of
isoquinolines and a source of detailed data for the frequent user.
Since the publication of Part One of the isoquinoline series in 1981, unfortun-
ate factors delayed publication of the intended Parts Two, Three, and Four,
which were originally targeted for the early 1980s. Because of the delay, the
chapters in Part Two differ from the projected ones indicated in the contents of
Isoquinolines: Part One.
We made a commitment in 1987 to see that the subsequent Isoquinolines
volumes were published as soon as possible. This volume is the result of the work
of authors who have been prompt in responding to our call to update their
chapters.
The present volume gives details of the chemistry of the following isoquinoline
derivatives: Halogenated and metallated isoquinolines and their hydrogenated
derivatives; isoquinoline carboxylic acids and their hydrogenated derivatives;
isoquinolines containing basic functions at the ring and their hydrogenated
derivatives; and isoquinolines containing oxidized nitrogen functions and their
hydrogenated derivatives. We wish to acknowledge our gratitude and appreci-
ation for the efforts of the authors who contributed to this volume, thus making
possible the expeditious publication of this book.
Many thanks are also given to the staff members of the library of Sandoz
Research Institute for their much-needed help. Joyce Birch and Ellen Brennan
have our appreciation and gratitude for their secretarial services. We also wish to
acknowledge the silent support of our family members during the hours spent on
editorial tasks.
F. G. KATHAWALA
GARYM . COPPOLA
HERBERF.T S CHUSTER
Sandoz Research lnsriture
East Hanover. New Jersey
May 1989
xi
Cont ents
1. Halogenated and Metallated Isoquinolines and Their Hydrogenated
Derivatives 1
M. D. NAlR and M. S. PREMILA
11. lsoquinoline Carboxylic Acids and Their Hydrogenated Derivatives
133
F. D. POPP and F. F. DUARTE
Ill. lsoquinolines Containing Basic Functions at the Ring and Their
Hydrogenated Derivatives 367
I. W. MATHISON and W. E. SOLOMONS
IV. lsoquinolines Containing Oxidized Nitrogen Functions and Their
Hydrogenated Derivatives 479
J. W. BUNTING
Index
533
...
Xlll
ISOQUINOLINES
PART TWO
771;si s rhe rhirry-eiyhrh colume in the series
THE CHEMISTRY OF HETEROCYCLIC COMPOUWDS
Chemistry of Heterocyclic Compounds, Volume3 8
Edited by F. G. Kathawala, Gary M. Coppola, Herbert F. Schuster
Copyright 0 1990 by John Wiley & Sons, Ltd.
CHAPTER I
Halogenated and Metallated
Isoquinolines and Their
Hydrogenated Derivatives
M. D. NAlR AND M. S. PREMILA
Pharmaceuticals Division, Southern Petrochemical Industries Corporation Limited, Madras, Indie
1. Introduction .................................................................. 3
11. Ring-Halogenated Isoquinolines __............ ..... 4
A. Methods of Synthesis., . . . . . . . . . . . . . . . . . , . . . , . , , . . . . . . . . . . . . . . . . . . . . . . . . . . . 4
(a) General _.._................ ........................... 4
(b) Halogenation of the lsoquinoline or its Salts, ..................... 4
(il Direct Halogenation . . . . . . . . . . . . , , . . . . . , . . . , . . . , . . . . . . . . . , , , . . . . . 4
(ii) Swamping Catalyst Method ........................... 6
(iii) Halogenation of Activated ............................... 8
(c) From N-Oxides . . , . . . . . . . . . . . . . . . . . , . . . , . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10
(i) Halogenation of N-Oxides . . . . . . . . . . . . 10
(d) C(1o1) nveRrseiaornra nofg eHmyednrtosx oyfi sNoq-Ouixniodleins e. s. .. .. .. ,. ,. .. .. ,, .. .. .. .. .. .. .. .. .. .. ,. .. .. .. .. .. .. .. .. .. ,. .. I. .. .. .. .. 1112
(e) Building Up of thc Pyridine Ring of Isoquinolines ...... 18
(i) Through Nitrilium Salts or Their Equivalents.. . . . . . . . . . . _.. . , . . . . . 18
(it) Pomeranz-Fritsch Synthesis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24
(iii) One-Step Perchloroisoquinolinc Synt hcsis . . . . . . . . . . . . . . . . . . , , 26
(0 Sandmeyer and Schiemann Reactions.. . . . . . . . . . . . . . . . . . . . . . . . . . . . . , . . . . 26
(i) Sandmeyer Reaction. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 26
(ti) Schiemann Reaction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 29
(g) Friedel Crafts-Type Ring Clowre . . . . . . . . . . . . . . . . . . , . . . . . . . . . . . . . . . . . . . 29
(h) Miscellancous Methods . ..................... 31
...I
(i) Rearrangements. ............................ ..._.._._._____3_1 ....
(ii) Replacement Reactions. . . . . . . . . . . . . . . , . . . . . . . . . . . . . . . . , , . . . , , . . , . 33
(iii) Cleavage Reactions ................. .... 34
(iv) lnterconversions . . . . . .. . . . . . . ._.,. . . , .. . . _.. . _... , __. ... . . ._.. . . 34
(v) Selective Reduction . . . . . . . . . . . . . . , . . , . . . . . . . . . . . . . . . . . . . . . . . . . . . 35
(vi) Other Methods.. . . . . . . . . . . . ....... ........ ............. 36
B. Bromoisoquinolines ........ ........................ .... ..._ .. _.. .__,.. .... 38
C. Chloroisoquinolines ....................................................... 40
D. Fluoroisoquinolincs .......................................................
40
E. lodoisoquinolines ......................................................... 41
F. lsoquinolines Substituted by Direrent Halogens . , . . . . . . . . . , . . . . . . . , . . . . . . . . . 41