Mt. Cocco et al., A facile synthesis of 3,5-diaminopyrazole-4-carbothioamides and 3,5-diaminopyrazole-4-carboxylates, J HETERO CH, 36(5), 1999, pp. 1183-1188
Simple and convenient synthesis of hitherto unknown 3,5-diaminopyrazole-4-c
arbothioamides 3 as well as new ethyl 3,5-diaminopyrazole-4-carboxylates 7
is reported. The key intermediates were 2-cyanopropenethioamides 2 and 2-(e
thoxycarbonyl)propene thio amides 5 which were readily obtained by reaction
of phenyl isothiocyanate with 3-(2-acylhydrazino)-3-aminopropenenitriles 1
and ethyl 3-(2-acylhydrazino)-3-aminopropenoates 4 respectively. Intramole
cular cyclization of compounds 2 afforded pyrazole-4-carbothioamides 3 whil
e propenethioamides 5 gave pyrazole-4-carboxylates 7.