Cyanide as a powerful catalyst for facile synthesis of benzofused heteroaromatic compounds via aerobic oxidation

Abstract

Highly efficient synthesis of benzofused heteroaromatic compounds via aerobic oxidation catalyzed by cyanide anion has been developed. The Schiff bases derived from 2-aminophenol and aldehydes provided the corresponding benzoxazoles in high yields in the presence of a catalytic amount of cyanide in an open flask under ambient conditions without the use of any external metal co-oxidants and bases. Furthermore, we have developed a catalytic sequential one-step protocol for the synthesis of benzoxazoles by adding a catalytic amount of NaCN to Schiff bases generated in situ from 2-aminophenol and aldehydes without the isolation of imine intermediates. This one-pot protocol was further extended to the synthesis of benzothiazoles from 2-aminothiophenol and aldehydes. A variety of aldehydes could be applied to this sequential one-pot protocol and the desired benzofused azole products were obtained in high yields. (C) 2013 Elsevier Ltd. All rights reserved.