Synthesis and Cyclization Reactions of 2-Amino-3-[(methoxycarbonyl)methylsulfonyl]pyrroles and Thiophene

The title aminopyrroles and thiophene have been prepared by condensation of methyl (cyanomethylsulfonyl)acetate with various α-amino ketones or 2-mercaptoacetaldehyde, respectively. Subsequent cyclization of these compounds by reaction between the amine and activated methylene has led to various ester-substituted thiazine- and thiadiazine-based bicyclic derivatives. In addition, cyclization of the title compounds by intramolecular coupling of the amine and ester has led to the analogous bicyclic thiazin-3(2H)-ones. Attempted hydrolysis of the ester-substituted bicyclics to the corresponding carboxylic acids was unsuccessful.