Collect. Czech. Chem. Commun. 1981, 46, 436-445

Synthesis of 2-substituted 5-arylidenethiazolin-4-ones from α,β-unsaturated acyl isothiocyanates

Peter Kutschya, Milan Dzurillab, Pavol Kristianb and Kvetoslava Kutschyováb

a Department of Organic Chemistry, Slovak Institute of Technology, 880 37 Bratislava
b Department of Organic Chemistry and Biochemistry, P. J. Šafárik University, 041 67 Košice


α,β-Unsaturated acyl isothiocyanates react with N-methylaniline to give thioureas which, when treated with bromine in chloroform, afford benzothiazoline derivatives. Under the same reaction conditions primary amines, diethylamine, piperidine and morpholine furnish 2-substituted 5-arylidenethiazolin-4-ones. Their structure was corroborated by an independent synthesis and on the basis of spectral (IR, 1H-NMR and mass) evidence.