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Chapter 3
Synthesis of trisubstituted pyrazoles/isoxazoles
Spectral data of the synthesized compounds
3-Cyclopropyl-N-(4-fluorophenyl)-3-oxopropanamide 3c.White solid; R f 0.42 (8:2
hexane-EtOAc); IR (KBr): 3364, 2927, 1674, 1533, 1462, 1281, 1112, 873 cm -1 ; 1 H
NMR (300 MHz, CDCl 3 ): δ 1.07-1.13 (q, 2H, CH 2 ), 1.14-1.20 (q, 2H, CH 2 ), 2.00-
2.06 (m, 1H, CH), 3.71 (s, 2H, CH 2 ), 6.97-7.03 (m, 2H, Ar-H), 7.48-7.53 (m, 2H, Ar-
H), 9.43 (s, 1H, NH); MS (m/z): 221 (M + ); Anal. Calcd for C 12 H 12 FNO 2 : C, 65.15; H,
5.47; N, 6.33; Found: C, 65.17; H, 5.45; N, 6.34.
N-(4-chlorophenyl)-2-(cyclopropylcarbonyl)-3,3-bis(methylsulfanyl)prop-2-
enamide 4b. Yellow solid; R f 0.48 (8:2 hexane-EtOAc); IR (KBr): 3033, 2927, 1674,
1533, 1462, 1281, 1112, 873 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 1.02-1.06 (m, 2H,
CH 2 ), 1.21-1.24 (m, 2H, CH 2 ), 2.37-2.43 (m, 1H, CH), 2.47 (s, 6H, 2xSCH 3 ), 7.26-
7.29 (d, 2H, j=9.6Hz, Ar-H), 7.53-7.59 (d, 2H, j=8.7Hz, Ar-H), 8.69 (s, 1H, NH); MS
(m/z): 342 (M + ); Anal. Calcd for C 15 H 16 ClNO 2 S 2 : C, 52.70; H, 4.72; N, 4.10; Found:
C, 52.72; H, 4.75; N, 4.12.
2-(Cyclopropylcarbonyl)-N-(4-methoxyphenyl)-3,3-bis(methylsulfanyl)prop-2-
enamide 4d. Yellow solid; R f 0.42 (9:1 Chloroform: Methanol); IR (KBr): 3364,
2927, 1674, 1533, 1462, 1281, 1112, 873 cm -1 ; 1 H NMR (400 MHz, CDCl 3 ): δ 1.02-
1.04 (m, 2H, CH 2 ), 1.22 (m, 2H, CH 2 ), 2.39-2.42 (m, 1H, CH), 2.47 (s, 6H, 2x
SCH 3 ), 3.84 (s, 3H, OCH 3 ), 6.85-6.88 (d, 2H, j=8.7Hz,Ar-H), 7.48-7.51 (d, 2H,
j=8.7Hz,Ar-H), 8.35 (s, 1H, NH); MS (m/z): 337 (M + ); Anal. Calcd for C 16 H 19 NO 3 S 2 :
C, 56.95; H, 5.68; N, 4.15; Found: C, 56.92; H, 5.65; N, 4.12.
3-Cyclopropyl-5-(methylthio)-N-p-tolyl-1H-pyrazole-4-carboxamide 5a. White
solid; R f 0.71 (9:1 Chloroform: Methanol); mp 155-157 o C; IR (KBr): 3284, 3151,
3083, 3031, 2968, 2841, 1628, 1586, 1408, 1238, 1037, 887, 834 cm -1 ; 1 H NMR (300
MHz, CDCl 3 ): δ 0.81-0.82 (m, 2H, CH 2 ), 0.96-0.99 (m, 2H, CH 2 ), 2.24 (m, 1H, CH),
2.40 (s, 3H, CH 3 ), 2.48 (s, 3H, SCH 3 ), 7.09-7.11 (d, 2H, j=8.1Hz, Ar-H), 7.51-7.53
(d, 2H, j=8.1Hz, Ar-H), 9.36 (s, 1H, NH), 12.84 (s, 1H, NH); MS (m/z): 287 (M + );
Anal. Calcd for C 15 H 17 N 3 OS: C, 62.69; H, 5.96; N, 14.62; Found: C, 62.68; H, 5.95;
N, 14.62.
Department of Chemistry Saurashtra university, Rajkot-360005 103