Merging the ring opening of benzoxazoles with secondary amines and an iron-catalyzed oxidative cyclization towards the environmentally friendly synthesis of 2-aminobenzoxazoles

Literature Information

Publication Date 2013-08-06
DOI 10.1039/C3GC41206G
Impact Factor 10.182
Authors

Daqian Xu, Wenfang Wang, Chengxia Miao, Qiaohong Zhang, Chungu Xia, Wei Sun


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Abstract

A facile and environmentally friendly method was developed through merging the ring opening of benzoxazoles with secondary amines and an iron-catalyzed oxidative cyclization towards the synthesis of 2-aminobenzoxazoles. In the oxidative cyclization step, with catalytic amounts of FeCl and aqueous H2O2 as a green oxidant, highly desirable 2-aminobenzoxazoles were isolated in excellent yields of up to 97%. A plausible radical process is proposed for the oxidative cyclization on the basis of mechanistic studies.

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