Chemistry of Heterocyclic Compounds: Pyridine and its Derivatives, Part 5, Volume 14

719 Pages·1985·15.852 MB·English

PYRIDINE AND ITS DERIVATIVES
Part Five
This is the jourteetith iw/ut?ii, in the siviips
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
___-
- - _-_ ._-._- _*-l_ll_---.-----_ --
TItE OF HETEROCYCLIC COMPOUSDS
CHEMISTRY
A SERIES OF MONOGRAPHS
ARNOLD WEISSBERGKR AND EDWARD C. TAYLOR
@
PYRIDINE AND
ITS DERIVATIVES
Part Five
Edired by
George R. Newkome
Louisiana State University
Baton Rouge. Louisiana
AN INTERSCIENCE PUBLICATION
"I
John Wiley and Sons
NEWYORK CHICHESTER BRISBANE TORONTO SINGAPORE
____I______II____ _-I_-_.---- c._-_-.- -__ll____l_I____ _____.__ ___ __X_I__._-.--.--_
An Interdencc " PUbllCdtioll
Copyright @ 1984 hy John Wiley & Sons. Inc.
All rights rewved. Puhlished simultaneously in Canada.
Keproductioii or translalion of any part of this work
beyond that permitied by Section 107 or 108 ofthe
1976 United States Copyright Act without the permission
of ihe copyright owner is unlawful. Requests for
permishn or further information should be addreshed to
the Periniwons Department. John Wiley & Sons. Ins.
Library of Congrclr.5 catabging in Publication Data :
( Revid Ibr volume 5)
Klingsberg. Erwin.
Pyridine and it\ derivatives.
(The Cheniislr) of heteroc)clic ccimpound>: a ,cries
of nionographs. v. 14)
5- edited hy George R. Newkoiiir
Vd.
Vd. 5- ha3 impriiir : New York : Wile!
"An Interscience publication" -Val. 5. I p
Include\ hihl iograph ics.
I. Plridiiie. I. Ncwkoine. George R. (George Kizh.irdI
II. Title. Ill. Serie\: Chemistry of heieroc?clic
compound>.\ . 14.
QD4Oi.K712 547'.5Y3
59-13038
ISBN 0-471-05072-5 (v. 5)
10 9 7 6 5 4 3 2 i
K
Contributors
T. D. BAILEY J. D. SAUER
Reilly Tar and Chemical Corporation Ethyl Corporation
Indianapolis, Inilianu Baton Rouge, Louisiana
G. L. GOE E. F. V. SCRIVEN
Reilly Tar and Chemical Corporation Reilly Tar and Chemical Corporation
Indiunapolis, Indianu Indiarwpolis, Indiana
V. K. GUPTA R. P. THUMMEL
Depa r ttnen t of' Clierii is try Depar frnent 01' Client istry
Louisiana Stute Uniwrsity Unicersity of' Houston
Baton Roicyr, Louisium Houston. Trsas
G. R. NEWKOME
Department of Clietnistry
Louisiana Stare Unioersitj
Baton Rouge, Louisiarru
Tbe 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, how-
ever, 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.
Researcli Lubornrories ARNOLDW EISSBERGER
h s m mK oahk Compnny
Roclrester, New York
Princeton Uiiiixvsify EDWARDC . TAYLOR
Princeton, New Jersey
vii
Preface
The original four volumes of this pyridine series were published between 1960
and 1964 under the guidance of Dr. Erwin Klingsberg. In 1974-1975, Professor
Rudy Abramovitch edited a four-volume supplemental series, which followed
the general format of the initial work. These herculean tasks covered most of
the important research in pyridine chemistry up to 1970-1972.
As with most areas of organic chemistry, proliferation has occurred at an
incredible rate, especially in heterocyclic chemistry. The need for a topical
update in key research areas is essential ; thus, the supplemental series has
changed format in order to keep the interest in pyridine chemistry as current as
possible.
In 1977, Professor Abramovitch and I discussed the creation of this ex-
pansion of Pyridine and Its Derivatiues and decided to abandon the difficuli-
to-organize chapter order of the previous volumes in this series. Also, new
topics and directions caused duplication and a need for new chapters to meet
the ever-expanding field of pyridine chemistry. As the task started, Professor
Abramovitch’s writing and editing obligations in other areas of interest pre-
vented his devotion to this series; his efforts are sorely missed.
This and all future supplementary volumes in the Pyridine and Its Derimriucs
series will be devoted to specific areas of interest and will attempt to remain
as the comprehensive repository of pyridine chemistry.
I express my thanks to the authors for their contributions and patience as
well as to Abramovitch for his initial guidanceand support in this project.
Rudy
GEORGE NEWKOME
R.
ix
Contents
I. SYNTHETIC AND NATURAL SOURCES OF THE 1
PYRIDINE RING
T. D. BAILEYG, . L. GOE,a nd E. F. SCRIVEN
V.
11. CARBOCYCLIC ANNELATED PYRIDINES 253
R. P. THUMMEL
111. MACROCYCLIC PYRIDINES 447
G. NEWKOMEV, . K. GUPTAa,n d J. D. SAUER
K.
IV. THE REVIEWS OF PYRIDINE CHEMISTRY-11968-1982 635
G. R. NEWKOME
AUTHOR INDEX 659
SUBJECT INDEX 703
xi
PYRlDlNE AND ITS DERIVATIVES
Part Five
This is tl~efourttwi~Iloi htnrc it1 [lie .seric.y
THE CHEMISTRY OF HETEROCYCLIC COMPOUNDS
Chemistry of Heterocyclic Compounds, Volume 14
Edited by George. R. Newkome
Copyright 0 1984 by John Wiley & Sons, Inc.
CHAPTER I
Synthetic and Natural Sources
of the Pyridine Ring
BAILEY, G. COE, and SCRIVEN
T. D. L. E. F. V.
Reilly Tar and Chemical Corporation, Indianapolis, Indiona
I. Pyridines from Natural Sources . . . . . . . . . . . . . . . 3
. . . . . . . . . . . . . . . . . .
1. Pyridines in Nature 3
A. Enzymes, Vitamins, Amino Acids, and Their Biogenesis . . . . . . 3
B. The Tobacco Alkaloids. . . . . . . . . . . . . . . . I
. . . . . . . .
C. Other Pyridine Alkaloids and R.ela.ted. Co.mp.oun.ds . . . . . . . . 11
a. Simple Pyridine Alkaloids . . . . . . . . . . . . . . 11
b. Monoterpenoid Alkaloids 12
. . . . . . . . . . . . .
c. Scsquiterpenoid Alkaloids 16
. . . . . . . . . . . .
i. Derivatives of Nicotinic Acid 16
. . . . . . . . . .
ii. Pyridone and Pyridinol Alkaloids. 11
iii. Other Sesquiterpcnoid Alkaloids . . . . . . . . . . . 22
. .
d. pCarboline and Related Alkaloids That Contain a Pyridinc Ring. 23
. . . . . . . . . . . . . .
2. Degradation of Natural Products 24
A.Coa1. . . . . . . . . . . . . . . . . . . . .
B. Petroleum . . . . . . . . . . . . . . . . . . . 24
. . . . . . . . . . . . . . . . . . . . 28
C. Shale.
. . . . . . . . . 29
D. Degradation and Transformation of Alkaloids . . . 31
E. Flavors, Odors, and Vol.atil.e Co.ns.titu.ent.s of .Fo.od a.nd. Be.vera.ges. . . . 33
F. Miscellaneous Sources 36
. . . . . . . . . . . . . . .
11. Pyridines by Synthetic Methods 36
1. From Other Ring Systcms . . . . . . . . . . . . . . . . 36
A. Carbocyclic Compounds . . . . . . . . . . . . . . . 31
B. Three-Membered Ring Heterocycles . . . . . . . . . . . . 43
. . . . . . . . . . . .
C. Four-Membered Ring Heterocycles 46
. . . . . . . . . . . .
D. Five-hlcrnbered Ring Heterocyclcs 41
a. Fi. iveF-uMreamnsb, eDre.ihd yRd.irnogf.us rCa.onns,t. aainndi.n Tge .Otrnae.h yIlde.rtoefr.uoraatno.sm .. ... ... ... ... ... ... 4488
ii. Pyrroles 55
b. Five-Membered Rings Containing Two Heteroatoms . . . . . . 60
i. Oxazoles. . . . . . . . . . . . . . . . . . 60
ii. Miscellaneous Fivc-hlembered Ring Hetcrocycles . . . . . . 68
E. Six-Mcmbered Ring Heterocycles. . . . . . . . . . . . . I5
a. One Heteroatom . . . . . . . . . . . . . . . . I5
i. Pyrones . . . . . . . . . . . . . . . . . . I5
1