Chemistry of Heterocyclic Compounds. Volume 32. Quinolines. Part II

690 Pages·33.18 MB·english

by  Jones G.

QUINOLINES
Part
I1
This i.7 the rhirrv-second volume in [he series
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
_-
._-__._ _._~_- ..._. _.. . .. . . . ------ .._ . ... .. .. -. --. --,-..-...---,---.- -
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
A SERIES OF MONOGRAPHS
ARNOLD WEISSBERCER and EDWARD C. TAYLOR
Editors
- -- . --_- -..--------_ - __I-..-.-- --- .-.-----I
Q U I N O L I N E S
Part I1
Edited by
Gurnos Jones
DEPARTMENT OF CHEMISTRY
UNIVERSITY OF KEELE
STAFFORDSHIRE
AN INTERSCIENCE@ PUBLICATION
JOHN WlLEY &
- SO- NS
CHICHESTER NEW YORK BRISBANE TORONTO SINGAPORE
* *
An Interscience@ Publication
Copyright (. 1982 by John Wiley & Sons Ltd
All rights reserved.
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 Caidoging in Publication Data I Revi.sed)
Main entry under title:
Quinolines
(The Chcmistry of hctcrcxjclic compounds; v. 32)
"An Interscience publicaticn."
Includes hihliographiwl relerences and indexes.
I. Quinoline. I. Jones. Gurnos.
QD4OI.Q56 547'.596 76- 26941
ISBN 0471 99437 5 (v. I) AACRI
British Library Caidoguing in Pub!ication Data.
Quinolines.
Part 2.4The chemistry of heterocyclic
compounds. v.32)
1. Jones. Gurnos JI. Series
547'.5% QD40 I
ISBN 0 471 28055 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 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 EISSBERGER
Reseurclt LuhoruroriPs
Eustmun Kohk Conipunj
Rocliesfer. New York
EDWARDC . TAYLOR
Princeton University
Princeton. New Jersey
V
Preface
The second part of the volume dealing with the chemistry of quinolines follows the
pattern of the first. Every effort has been made to present a comprehensive coverage of
the three classes of compound dealt with. A slight departure from the normal procedure
has been necessary in Chapter 3, where over 300 references to purely biological
properties of the N-oxides have been grouped as a bibliography. As in the first part,
tabulated compounds are not generally entered in the subject index.
One of the authors A. C.) is indebted to the City University for leave of absence to
(P.
enable the final stages of the work to be completed in a reasonable time. He, and I. also
thank our wives for help given during the preparation of the manuscripts.
GURNOJSO NES
University oj Keele
Slagordshire
vii
List of Contributors
BATY,J . D. Department of Biochemical Medicine, University of Dundee.
Dundee, UK
CLARETP., A. Department of Chemistry, City University. London. UK
JONES, G. Department of Chemistry. University of Kccle. Keele.
Staflrdshire , U K
OSBORNEA,. G. Department of Chemistry, City University. London. UK
POPP,F . D. Department of Chemistry, University of Missouri-Kansas City,
Kansas City, Missouri, USA
ix
Contents
. . . . . . . .
1 Alkylquinolines and Arylquinolines 1
P . A . CLARET and A . c . OSBORNE
. . . .
2 Reissert Compounds and Related N-Acyldihydroquinoliws 353
. .
F D POPP
. . . . . . . . . . .
3 Quinoline N-Oxides 377
c . JONES and D . J . BATY
. . . . . . . . . . . .
Author Index
607
. . . . . . . . . . . .
Subjectlndex 659
xi
Chemistry of Heterocyclic Compounds, Volume3 2
Edited by Gumos Jones
Copyright 0 1982 by John Wiley & Sons, Ltd.
.
Quinolines Part II
Edited by G . Jones
.
1982. John Wiley & Ltd
i Sons
CHAPTER 1
Alkylquinolines and Arylquinolines
. .
PAUL A CLARET and ALAN OSBORNE
G
. . .
Depurtment of Chemistry The Cirv Universitv Northumpton Square. London ECIVOHB UK
1. Alkylquinolines and Aralkylquinolines . . . . . . . . . 6
I . Preparation by Pyrolysis and Degradation of Natural Products . . . . 6
2. Synthesis from Compounds Not Containing a Quinoline Ring System . . . 8
3. Synthesis from Compounds Containing a Quinoline Ring System . . . .
9
A . Reduction Methods . . . . . . . . . . . . 9
a . Reduction of Halogen Derivatives . . . . . . . . 9
b . Reduction of Hydroxy and Amino Derivatives . . . . . . 10
c . Reduction of Carbonyl Compounds . . . . . . . . 1 1
d . Reduction of Alkenyl and Aralkenylquinolines . . . . . . 12
e . Reduction of Quinoline-I-oxides . . . . . . . . . 1 3
. Catalytic Alkylation . . . . . . . . . . . 1 4
B
C . Alkylation by Means of Organometallic Reagents . . . . . . 1 5
a . Nuclear Alkylations . . . . . . . . . . . 1 5
b . Sidechain Alkylations and Arylations . . . . . . . 18
D . Homolytic Alkylation . . . . . . . . . . . 1 8
E . Decarboxylation . . . . . . . . . . . . 2 1
F . Ladenburg Rearrangement . . . . . . . . . . 22
G . Oxidation of Dihydro- Tetrahydro- and . . . 22
Decahydroalkylquinolines
H . Miscellaneous Methods . . . . . . . . . . . 2 4
a . Molecular Rearrangements . . . . . . . . . . 2 4
b . Photochemical Methods . . . . . . . . . . 2 4
c . Aromatization . . . . . . . . . . . . 25
d . Nucleophilic Displacement of Halogen . . . . . . . 2 5
e . Ring Enlargement of lndoles . . . . . . . . . 2 6
f . Catalytic Side-chain Alkylation . . . . . . . . . 2 6
g. Side-chain Benzylation . . . . . . . . . . 26
h . Condensation with Qinoline-2-Carbaldehyde . . . . . . 27
i . Alkylation with Fatty Acids . . . . . . . . . 27
j . Alkylation of Reissert Compounds . . . . . . . . 2 7
.
4 . Physical Properties Uses and Methods of Separation . . . . . . 2 7
A . General Physical Properties . . . . . . . . . . 2 7
a . Melting Points and Boiling Points . . . . . . . . 2 7
b . Dissociation Constants . . . . . . . . . . 2 8
c . Dipole Moments . . . . . . . . . . . . 29
d . Surface Tension . . . . . . . . . . . . 2 9
e . Solubility . . . . . . . . . . . . . 29
f . Magnetic Susceptibility . . . . . . . . . . 30
g . Adiabatic Compressibility . . . . . . . . . . 30
B. Acidity of Sidechain Hydrogens . . . . . . . . . 30
I
2 Alkylquinolines and Arylquinolines
C . Stereochemical Properties . . . . . . . . . . 31
D . Biological and Pharmacological Properties and Medical Applications . . 31
E . Mixellaneous Properties and . . . . . . . . . 32
Uses
F . Analysis of Alkylquinolines . . . . . . . . . . 33
G . Spectroscopic Properties . . . . . . . . . . . 33
a . Electronic Spectra . . . . . . . . . . . 33
b . infrared Spectra . . . . . . . . . . . . 34
c . Nuclear Magnetic Resonance Spectra . . . . . . . . 34
d . Mass Spectra . . . . . . . . . . . . 47
H. Methods of Separation . . . . . . . . . . . 48
.
a . Distillation Crystallization and Counter-current Extraction . . . 48
b. Chromatographic Methods . . . . . . . . . . 49
5 . Chemical Properties and Reactions . . . . . . . . . 51
A . lsomerization and Dealkylation . . . . . . . . . 51
B. Oxidation . . . . . . . . . . . . . 51
a . Oxidations Leading to Ring Opening . . . . . . . . 51
b . 07onolysis . . . . . . . . . . . . . 52
c . Oxidation of Side-chains . . . . . . . . . . 53
d . Oxidation of Methyl Substituents to Aldehydes . . . . . . 56
e . Dehydrogenation OfTetrahydroacridines . . . . . . . 56
f . Oxidation to ,V- Oxides . . . . . . . . . . 57
g . Miscellaneous Oxidation Reactions . . . . . . . . 58
C . Reduction . . . . . . . . . . . . . 58
a . Dihydroalkylquinolines . . . . . . . . . . 58
b . Tetrahydroalkylquinolines . . . . . . . . . . 59
c . . . . . . . . . . . 62
Decahydroalkylquinolines
d . Miscellaneous Reductions . . . . . . . . . . 63
D. Ring-opening Reactions . . . . . . . . . . . 64
E . Side-chain Substitutions . . . . . . . . . . . 66
a . Deuterium and Tritium Exchange . . . . . . . . 66
. Side-chain Metalation and Alkylation . . . . . . . . 66
cb . Side-chain Halogenation . . . . . . . . . . 67
d . Miscellaneous Side-chain Substitutions . . . . . . . 68
F . Nuclear Substitutions . . . . . . . . . . . 12
a . Deuterium Exchange . . . . . . . . . . . 73
b . Nitration . . . . . . . . . . . . . 73
c . Sulphonation . . . . . . . . . . . . 74
d . Halogenation . . . . . . . . . . . . 75
c . Mcrcuralion . . . . . . . . . . . . 71
f . FriedelLCrafts Substitutions . . . . . . . . . 78
g . Amination . . . . . . . . . . . . . 78
h . Hydroxylation . . . . . . . . . . . . 78
i . Alkylation and Aryldtion . . . . . . . . . . 79
. Homolytic Kuclear Substitutions . . . . . . . . 79
j
G . Addition Reactions . . . . . . . . . . . . 81
a . General Addition Reactions . . . . . . . . . 81
b . Reissert Reaction . . . . . . . . . . . 82
H . Syntheses of Condensed Ring Systems . . . . . . . . 84
1. Condensation Reactions . . . . . . . . . . . 88
a . Condensations with Aldehydes and Ketones . . . . . . 88
b . Condensations with Esters . . . . . . . . . . 91
c . Condensations with Phthalic Anhydride and Related Derivatives of Di- a nd
Polycarboxylic Acids . . . . . . . . . . . 91
d . Condensations with Amines and Sulphur; Willgerodt-Kindler Reaction . 93
J . Photochemical Reactions . . . . . . . . . . . 95
. Salt Formation and Complexes . . . . . . . . . 96
K
a . Quaternary Salts . . . . . . . . . . . . 96
b . Charge-transfer Complexes . . . . . . . . . . 96