A facile synthesis of 3,5-diaminopyrazole-4-carbothioamides and 3,5-diaminopyrazole-4-carboxylates

Citation
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
Citations number
13
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
JOURNAL OF HETEROCYCLIC CHEMISTRY
ISSN journal
0022152X → ACNP
Volume
36
Issue
5
Year of publication
1999
Pages
1183 - 1188
Database
ISI
SICI code
0022-152X(199909/10)36:5<1183:AFSO3A>2.0.ZU;2-U
Abstract
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.