sodium dichloroiodate promoted c-c bond cleavage: an efficient synthesis of 1,3-benzazoles via condensation of o -amino/mercaptan/hydroxyanilines with β -diketones

An efficient aqueous sodium dichloroiodate (naicl 2) mediated protocol is developed for the synthesis of benzofused azoles by the cyclization of 2-amino anilines/thiophenols/phenols with β-diketone compounds. the reactions gave moderate to good yield of the corresponding 2-substituted benzimidazoles/benzothiazoles/benzoxazoles under mild conditions. this tandem process involved a c-c bond cleavage and c-n bond formation. graphical abstract : synopsis a facile and single protocol for the synthesis of three versatile 1,3-benzazoles viz 2-substituted 1h-benzimidazoles, benzoxazoles and benzothiazoles from readily available starting materials, 1,3-diketones and corresponding o-amino anilines/thiophenols/phenols, by aqueous sodium dichloroiodate (naicl 2) mediated c—c bond cleavage has been developed. the reaction provides a rapid access to these 1, 3-benzazoles in good yields, thus speeding up the drug discovery process.[figure not available: see fulltext.]. © 2018, indian academy of sciences.