Different specificities in the bromination of 6-(2-furyl)imidazo[2,1-b]thiazole and its derivatives with 1 mole of bromine

Abstract

The action of 1 mole of bromine on 6-(2′-furyl)imidazo[2,1-b]thiazole, its 2-methyl-, 3-methyl-, and 2,3-dimethyl-substituted derivatives, and their hydrobromides in chloroform and glacial acetic acid was studied. The bromination of bases containing a methyl group in the 3 position leads primarily to the 5′-derivatives with respect to the furan ring in chloroform, whereas in the remaining cases 5-bromo derivatives with respect to the imidazothiazole system are formed. Compounds of the latter type are formed by the action of bromine in glacial acetic acid or of sodium hypobromite in alkaline media on the bases. The hydrobromides are brominated in both acetic acid and chloroform, regardless of the substituents in the thiazole ring, primarily in the 5′ position of the furan ring. The structures of the bromination products were proved by means of alternative syntheses, thin-layer chromatography, and the PMR spectra.