Collect. Czech. Chem. Commun. 1981, 46, 1160-1166

Synthesis and reactions of cis-3-(2-furyl)propenoyl isocyanate

Peter Kutschya, Pavol Kristianb, Miloslava Dandárováa and Jaroslav Kováča

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


cis-3-(2-furyl)propenoyl isothiocyanate has been synthesized and its properties have been compared with those of the trans-isomer. Treatment of the foregoing isothiocyanates with benzylamine, piperidine or diazomethane yielded the corresponding thiourea and thiadiazole derivatives having unchanged configuration. Oxidation of the thiourea derivatives with bromine, or reaction of the isomeric isothiocyanates with NaSH and diphenylamine is independent of the configuration of the starting substances: the same thiazoline or perhydro and dihydrothiazine derivatives are formed. It has been concluded, based on 1H and 13C-NMR data that, relative to the C=C bond, the furan ring in cis- and trans-3-(2-furyl)propenoyl derivative exists in s-cis and s-trans conformation, respectively.