Reaction of [beta]-Bromo-[beta],[gamma]-unsaturated Pyrroline Nitroxide Aldehydes and Nitriles with Aromatic N,S-Binucleophiles

Reactions of [beta]-bromo-[beta],[gamma]-unsaturated pyrroline nitroxide aldehyde (1) or nitrile (4) or their diamagnetic forms (5, 6) with 2-aminothiophenol or 2-mercaptobenzimidazole were evaluated. The reaction could be reproduced more easily with the application of O-acetyl derivatives of nitroxides to generate 2-substituted-benzothiazole, pyrrolo[3,4-b]benzo[1,5]tiazepine scaffolds with 2-aminothiophenol and benzimidazo[2,1-b]pyrrolo[3,4-e]-[1,3]thiazine scaffold with 2-mercaptobenzimidazole.