Intramolecular oxidative deselenization of acylselenoureas: a facile synthesis of benzoxazole amides and carbonic anhydrase inhibitors. Issue 48 (28th November 2016)

• Record Type: Journal Article
• Authors: Angeli, A.; Peat, T. S.; Bartolucci, G.; Nocentini, A.; Supuran, C. T.; Carta, F.
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 48(2016)
• Page Start: 11353
• Page End: 11356
• Publication Date: 2016-11-28
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob02299e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A mild, efficient and one pot procedure to access benzoxazoles using easily accessible acylselenoureas as starting materials has been discovered. Abstract : A mild, efficient and one pot procedure to access benzoxazoles using easily accessible acylselenoureas as starting materials has been discovered. Mechanistic studies revealed a pH dependent intramolecular oxidative deselenization, with ring closure due to an intramolecular nucleophilic attack of a phenoxide ion. All the benzoxazoles herein reported possessed a primary sulfonamide zinc binding group and showed effective inhibitory action on the enzymes, carbonic anhydrases.