Collect. Czech. Chem. Commun. 1984, 49, 2285-2294

Synthesis and properties of 4-amino-5-(5-X-2-furyl)thiazole derivatives

Gennadii D. Krapivina, Adolf Jurášekb, Jaroslav Kováčb and Vladimír G. Kul'nevicha

a Krasnodar Polytechnical Institute, 350 006 Krasnodar, U.S.S.R
b Department of Organic Chemistry, Faculty of Chemical Technology, Slovak Institute of Technology, 812 37 Bratislava, Czechoslovakia


Reaction of dipotassium cyanimidodithiocarbonate ((KS)2C=N-CN) with 5-X-furfuryl halogenides (X=NO2, CHO) and 4-nitrobenzyl bromide gives the substituted esters which, in alkali medium, gives the carbanions undergoing cyclization to 4-amino-5-(5-X-2-furyl)thiazoles and 4-amino-5-(4-nitrophenyl)-2-(4-nitrobenzylthio)thiazole, respectively. Reaction of 5-X-furfuryl halogenides or 4-nitrobenzyl bromide with potassium methyl cyanimidodithiocarbonate (KSC(SCH3)=N-CN) gives the esters which are cyclized to 4-amino-2-methylthio-5-substituted thiazoles. The starting esters with X = COOCH3 give no carbanion and undergo no cyclization under the same conditions. The 4-amino group in the thiazole is easily acylated and diazotized, but it does not undergo alkylation. 1H NMR, UV, and IR spectra of the compounds prepared are discussed.