J o u v m l of illedicinul Chernistry, IY7'0, 1'01. 13, S o .
so11 h
4
781
TABLE I HISTICS O F 3 , j - L ) l ~ ~ E T H Y L - 4 - a R Y L . ~ Z O - ~ ' - ~ . ~ R ~ . I M O Y L P Y H . I Z o(Ia) LES
Yield,
%
X
3 0.
C:olorn
Mp, o c :
Formula
Analyses
I1N YO OC PeY N PeYN YN PeYPi YS PeYlr; PeYPi
C~2HuS603 ?; 210 CizHizS603 ?; 2 6r5 180- 18% CiJIizSeOa N J C12HizClNjO C1 60 156-1 57 4 3-c1 C12HizClNjO e1 70 159-160 ) 4-C1 65 143-144 Ci3HijNjO S 0 2-1Ie 55 163-164 Ci3HxSdI s i 4-1Ie 4 .5 1.33-154 CnHisN~j02 Pi S 2-OJte .io 141-142 CizHisXzOz !I 3-031e 60 164 CiaHiJVjOi N I I) 4-0Me .5O I .i9 It 2-OEt YS Ci,Hi;S:02 K 4.5 134-1 3 i YS CI~HL~XOZ x I2 3-OEt G !5 163 1 :: 4-OEt YC C14HiiNjOn ?: 14 4-SO2SITz .i ) ( 243-24.5 YN CI?H~~NE.O~S S Y Ci1HiiC12NsO e1 (i.5 228-229 1 r, 2,6-Clr 201-202 PeYS CiiHiiSsO s 16 2,5-.21ey ,iO 116-1 18 BN CirHiiKiOa ?; 17 2,3-(01Ie)t 0 Ci3Hi4ClNjO c1 18 2-Cl-G-lIe 60 188-189 B, brown; C, crystals; D, dark; G, golden; L, light; N, needles; 0, orange; P, plates; Pe, pale; R, red; Ru, rust; S, specks; Y, yellow. 1
5.5 50
"-SO2 3-KO1 4-NOz
204-20.5
I
x
--
*)e)
r IHLpd 11 CH LR I C 1 L R I S F I C S
OF
3-Atf.,PHYL-&.illYL iZO-5-PHENYL-.V1-C
5 leld,
h 0. 1
2 3 4 )
6
7 8
56 r,0
S
2-so2 3-KO2 4-C1 3-Me 4-Ale 2-011e 3-OJIe 4-OJle
--
d.)
65 60
--
.I.)
4i 30
GO 30
4-053 4-SOJNITJ 2,,.5-Cl2 :?,,i-JIez See footnote a of Table I. 0 10 11 1.2
a
--
I).)
65 GO
CH IR ICTI
s
NO.
1
Ph
2
2-xo2 %NO2
3 4
4-KOz 5 4-C1 G 2-3, e12 7 2,6-c12-4s02 a See footiiote a of Table I.
IZISITCS O F
Tield
hlp,
oc
LKU I V O Y L P Y R I Z O L E S
Cololn
206-207 18.5-187 197-198 177-178 166-167 1JO-13 1 1285-126 17-5-176 178-179
0 Y
24.3-246 243-24.5
0
192-193
(Ib)
Formula
Y LY PeY PeYK Y Y Y
CisHiiN,O
K
YO YN
s Pi
x N
Pi N
e1 N
T I H L I , 111 3,5-DIMb2rHYL-4-i R Y L i Z O - i ~ l - H I P P U R Y L P Y R i Z O L E S
LIP, oc
Cololn
133 265-267 dec 278-280 dec 278-280 dec 209-210 174-17;i 2 1 -5-2 16
GYS
CzoHi8sOz
OYP
C2oHl8~6O4 CZOH18~604
--
c1
CiaHi;N& Ci8H17SuOi CisHnNoOz CisHiiSsOz C19H19N502 CiiHi6N60zS Ci7Hi3C12N00 Ci9Hi9Xa0
70
I).)
N
N
63 60 6.i GO
70 7.5
Analyses
Ci7Hi4N603 CiiHi4N& CiiHiaClN,O
t o these' gave an incentive to search for new agents.2 Towards this end, we have synthesized three series of pyrazole derivatives, namely, 3,5-dimethyl-4-arylazoN '-carbamoyl- (Ia) , 3-methyl-4-arylazo-5-phenyl-N lcarbamoyl- (Ib), and 3,5-dimethyl-4-arylazo-N1-hippurylpyrazoles (IC). Precursors 2,3,4- pentanetrione 3 - arylhydra~ones~ (1) I). E. Delamater and J. AI. RIoss, J . dmer. M e d . A s s . , 181, 89 (1962); K . A . Carnerini-Davalos and A. Marble. ibid., 181, 176 (1962). Editorial, ibid., 181, 131 (1962). (2) H. G. Garg and P. P. Singh. J . Phnrm. Sci., in press and ref cited therein. (3) H. G. G a r g and P. P. Singli, J . .\led. Chem., 11, 1103 (1968).
Formula,
GP DYS
Analyses
N N
N ?;
K
I
la. K = R ' = M e ; R"=NH, 111. R = M e : R'=Ph; R"=NH2 IC, R = R ' = M e ; R=-CH:NH.Bz
R"C0
and l-phenylbutane-l,2,3-trione 2-arylhydra~ones~ were prepared by the condensation of diazotized anilines with 2,4-pentanedione and l-phenylbutane-1,3-dione, respectively. Hippuryl hydrazide was synthesized (4) 11. G. Garg and 1'. 1'. Singli, ,I. C h t m
SOC. c',
1141 (1969).
