CONDENSATION REACTIONS OF QUINOLINE-ALDEHYDES WITH ACTIVE METHYLENE COMPOUNDS

66 Pages·03.383 MB·English

by  PHILLIPS, ARTHUR PAGE

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.07 Phillips, Arthur Page, 1917-
]
1942 Condensation reactions of quinoline
* P4 aldehydes with active methylene com­
pounds... New York, 1942.
6p.l,,50 typewritten leaves, dlagr's.
29cm.
Thesis (Ph.9.) - New York university.
Graduate school, 1942.
Bibliography: p.49-50.
A84674
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Xerox University Microfilms, Ann Arbor, Michigan 48106
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OPIVEHCIIY HEIGHTS
Condensation Reactions of Quinoline Aldehydes
with Active Methylene Compounds
Submitted by
&
r?
Arthur Phillips
in partial fulfillment of
the requirements for
the degree of
Doctor of Philosophy
at
New York University
University Heights
June, 1942
ACKLO’.-.XSDC&ISNT
The author wishes to voice appreciation
to Professor H. G. Lindwall for his
patient direction during this research.
CCITTEI'iTS
Chapter I: Malaria and its Chemotherapy.................. ...
P u.r t X i-aluna. • . . * . «. . . . . . . # l
Part II Therapeutic agents used u0uinst Malaria . . . 2
Chapter II: Discussion ci t^e expsri—ental v.rork . . . . 7
Chapter III: Experimental .ork .................. £1
Hydantoin-5-quinoline-4-L.ethanol................ 21
Hydantoin-5-quinoline-2-nethuncl. . . . . . 22
5-{4-3uinolyluethylene)-2-t2iioh.ydantoin . . . 24
5-(2-^uinclylmethylene}-2-tkiohyduntoin . . . 25
3-(4-Q,uinoTylnstkylene Jburbituric acid . . . 26
Condense tion of .^uinoline-S-aldehyde -..itii
Barbituric acid ................ 26
5-(4-4'uinolylmethylene )-2-thiobarbituric acid . SO
5-(h-^uinolyl*..eth.ylene )-2-tniob'. r'oituric acid • SI
o
5-(4-iuinolyl„etiiylene)-i:7 S-diphenyl pseudo-
taio-hydantoin ........................ 32
p
6-(2-Q,uinolylmethylbrie )-12, S-diphenyl pseudo-
thio-hydantoin ......................... 34
5-(4-^uinolyliaethylene)-3-phenyl 2,4-diketo-
thiazolidine • • . « • • • » • .55
5-(2-quinolylmethylene)-3-phenyl-2,4-diketo-
thiazclidine ............................ 56
5-(4-^uinolylmethylene )-N-phenyl pseudo-
tliio-hydantoin.......................... 37
. , £
5-(2-£uinolyLaethylene)-K-phenyl pseudo-
tiiio-hydantoin . 38
5-(4-Q,uinolylnethylene )pseudo-thio-hydantoin. 39
5-(2-^uinolylnethylene} pseudo-thio-hydantoin 40
5-(4-:^uinolylLiethylene) riiodanine . . . . 41
5-(2-5,uinolylnethylene) rhodanine . . . . 42
2
o-iv.etnyl-1":, 3-diphenyl pseudo-thio-hydantoin-
3-q_uinoline-4-nethanol ................. 45
2
a-:.'etliyl-2, 3-dipnenyl pseudo-thio-hydantoin-
5-quinoline-2-methanol ............... 44
5-1 'ethyl -pseudo-tLio-liydantoin-5-(jui r oline-
4-uethanol ................ 45
5-i:etliyl-pseudo-thio-hydantoin-5-q>uinoline-2-
Liethanol................................ 46
Similar y .......................................................48
Bibliography......................... ................ 49
dTRODUCTION
INTRODUCTION
The purpose of this research has ben to synthesize
a series of new quinoline derivatives from the two active
aldehydes, cinchoninaldehyae and quinaldaldehyde.
Having in mind the desirability of obtaining com­
pounds of possible anti-malarial activity, these two
aldehydes have been condensed with a vide variety of
heterocyclic, as veil as some non-heterocyclic, active
methylene compounds, giving rise to products of unsaturated,
and in certain cases of the aldol type.
OHJPTIB I
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Ajm n *
CHAPTER I
1. ALAR IA AND ITS CHEXTHERAPY*
Part I Halaria
Ilalaria is an ancient malady having the greatest in­
cidence of infection of any germ disease. Predominantly
residing in the tropics it is, however, world vide in its
distribution.
The disease is caused by three species of plasmodia
(also there is an unimportant fourth variety) which form a
sub-group of parasitic, microscopic, unicellular animal or­
ganisms, having no locomotor organs. These organisms have
become adapted to an asexual life cycle in the circulating
red blood cells of certain vertebrates, the intermediate host,
and a sexual sojourn in the anopheles mosquito, the definitive
host.
*?he material of Chapter I of this thesis, introductory
to the experimental part, has been abstracted largely from
the following sources:
Goodman and Gilman, The Pharmacological Basis of Therapeutics
Hacmillan Co., New York, 1941— Chapter 50
Hegner, Root, Augustine, huff, Parasitology
Appleton, Century Co. Inc., New York 1958— Chapter 11
Hanson-Jahr, Hanson's Tropical Diseases
Williams and Nilkins Co., Baltimore, Haryland,
11 th Edition, 1940— Chapter 3
von Oettingen, Therapeutic Agents of the Q,uinoline Group
The Chemical Catalog Co. Inc., New York 1933
Chapter 7,8,11