Table Of ContentINFORMATION TO USERS
This malarial was produced from a microfilm copy of tha original documant. Whila
tha most advanoad technological means to photograph and reproduce this documant
have been used, tha quality is heavily dependent upon tha quality of tha original
submitted.
Tha following explanation of tachniquas is provided to help you understand
markings or patterns which may appaar on this reproduction.
1. The sign or "target" for pagas apparently lacking from tha documant
photographed is "Missing Pags(s)". If it was possible to obtain the missing
page(s) or section, they are spliced into the film along with adjacent pagas.
This may have necessitated cutting thru an image and duplicating adjacent
pages to insure you complete continuity.
2. When an image on the film is obiiteratad with a large round black mark, it
is an indication that the photographer suspected that the copy may have
moved during exposure and thus causa a blurred image. You will find a
good image of the page in the adjaoant frame.
3. When a map, drawing or chart, etc., was part of tha material being
photographed the photographer followed a definite method in
"sectioning" the material. It is customary to begin photoing at the upper
left hand comer of a large dieet and to continue photoing from left to
right in equal eactions with a small overlap. If necessary, sectioning is
continued agein - beginning below the first row and continuing on until
complete.
4. Tha majority of users indicate that the textual content is of greatest value,
however, a somewhat higher quality reproduction could be made from
"photographs" if essential to tha undarstandina of the dissertation. Silver
prints of "photographs" may be ordered at additional charge by writing
tha Order Department giving the catalog number, title, author and
specific pages you wish reproduced.
5. PLEASE NOTE: Soma pages may have indistinct print. Fiknad as
received.
Vmarikif I
AOTwl WsfWwljf M9GVWHVVW
sooNoteiiMenMtf
1V ItyW
LD3907
.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
" C)
' Shelf list
------------------------------------ — -i
Xerox University Microfilms, Ann Arbor, Michigan 48106
L7;T/PY OP
. BEI7 YCPK UljlVEPOITI
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
oarnvBstBOt
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
