Reaction of β-Bromo-β,γ-unsaturated Pyrroline Nitroxide Aldehydes and Nitriles with Aromatic N-Binucleophiles and S-Binucleophiles

Kálai, Tamás and Bognár, Balázs and Varga, Boglárka and Csokona, Viola and Sár, Cecília and Gulyás Fekete, Gergely and Hideg, Kálmán (2017) Reaction of β-Bromo-β,γ-unsaturated Pyrroline Nitroxide Aldehydes and Nitriles with Aromatic N-Binucleophiles and S-Binucleophiles. Journal of Heterocyclic Chemistry. ISSN 0022-152X, ESSN: 1943-5193 (In Press)

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Abstract

Reactions of β-bromo-β,γ-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.

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