Reactions of aromatic amines with 5-nitro-3-furoyl and 5-nitro-2-furoyl isothiocyanates

Abstract

5-Nitro-3-furoyl isothiocyanate reacts with 4-X-anilines (X = H, CH3, OH, N(C2H5)2, NHCOCH3, Cl, Br) to give the corresponding N-(5-nitro-3-furoyl)-N'-(4-X-phenyl)thioureas, in contrast to 4-methoxyaniline and 4-nitroaniline, which afford 5-nitro-3-furancarboxylic acid amides in a rather anomalous way. Formation of these amides is discussed and some properties of 2- and 3-substituted thioureas related to 5-nitrofuran are compared.