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Chapter 3
Synthesis of trisubstituted pyrazoles/isoxazoles
Table-1: 3-cyclopropyl, 5-methylthio, 4-carboxamide substituted pyrazoles and
isoxazoles.
Reaction time
Entry R Conventional
(hrs)
Yield
(%)
MW
(min.)
Yield
(%)
5a 4-CH 3 Ph 2.0 85 13.0 88
5b 4-ClPh 1.5 88 12.5 90
5c 4-FPh 1.5 87 10.0 92
5d 4-OCH 3 Ph 2.0 83 12.0 90
5e 3,4-diClPh 2.0 90 13.0 95
5f 3,Cl,4-FPh 1.5 85 12.5 88
5g 2,3-diCH 3 Ph 2.0 87 14.0 90
5h 4-NO 2 Ph 2.5 82 17.0 95
5i 2-OCH 3 Ph 1.5 85 14.5 97
5j 2-CH 3 Ph 2.0 83 13.0 93
5k 4-CH 2 CH 3 Ph 2.5 80 12.5 91
5l 5,Cl,2-OCH 3 Ph 2.0 82 13.5 95
5m 2,5-diClPh 1.0 87 12.0 90
5n 2,5-diCH 3 Ph 2.0 80 13.0 88
5o 3,4-diFPh 2.5 81 14.0 87
6a 4-CH 3 Ph 2.5 79 12.5 85
6b 4-ClPh 2.0 83 15.0 93
6c 4-FPh 3.0 82 14.5 90
6d 4-OCH 3 Ph 1.5 87 13.0 92
6e 3,4-diClPh 2.0 85 14.0 91
6f 3,Cl,4-FPh 2.5 82 13.0 87
6g 2,3-diCH 3 Ph 3.0 81 13.5 89
6h 4-NO 2 Ph 2.5 90 14.0 95
6i 2-OCH 3 Ph 3.0 89 15.0 94
6j 2-CH 3 Ph 2.5 87 17.5 92
6k 4-CH 2 CH 3 Ph 3.0 85 15.0 90
6l 5,Cl,2-OCH 3 Ph 1.5 80 12.5 84
6m 2,5-diClPh 1.0 88 13.0 96
6n 2,5-diCH 3 Ph 2.5 87 15.5 94
6o 3,4-diFPh 3.0 85 14.0 92
The structures of 4a-o were established on the basis of their elemental analysis
and spectral data (MS, IR, and 1 H NMR). The analytical data for 4b revealed a
molecular formula C 15 H 16 ClNO 2 S 2 (m/z 342). The 1 H NMR spectrum revealed a two
multiplet at δ = 1.02-1.06 and 1.21-1.24 ppm assigned two –CH 2 groups in
cyclopropane ring, a multiplet at δ = 2.37-2.43 ppm assigned to the –CH protons,
Department of Chemistry Saurashtra university, Rajkot-360005 97