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Synthesis and reactions of n-aryl-n'-(3-furoyl)thioureas

A. Jurášek, P. Šafařr, and V. Žvak

Department of Organic Chemistry, Slovak Technical University, CS-812 37 Bratislava

Abstract: 3-Furoyl isothiocyanate reacts with 4-X-anilines (X = H, CH₃, OH, OCH₃, N(C₂H₅)₂, NHCOCH₃, CI, Br, N0₂, COOH) under formation of the respective N-(4-X-phenyl)-N-(3-furoyl)thioureas. By treatment with bro­mine in acetic acid, thionyl chloride in chloroform, and methyl iodide in methanol, respectively, these thioureas do not cyclize to furo-fused deriva­ tives. In the reaction with bromoacetone and ú>bromoacetophenone they afford the corresponding 2-(4-X-phenylimino)-3-(3-furoyl)-4-R-4-thiazolines (R = CH₃,C₆H₅). The structures of the newly synthesized compounds were proved by IR, UV, ^IH NMR, and mass spectra.

Full paper in Portable Document Format: 415a693.pdf

Chemical Papers 41 (5) 693–702 (1987)