N-Bromosuccinimide as an oxidant for the transition-metal-free synthesis of 2-aminobenzoxazoles from benzoxazoles and secondary amines

A facile and transition-metal-free method was developed through merging the ring opening of benzoxazoles with secondary amines and N-bromosuccinimide (NBS) mediated oxidative cyclization toward the synthesis of 2-aminobenzoxazoles. NBS was selected as a powerful oxidant in the oxidative cyclization...

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Veröffentlicht in:Organic & biomolecular chemistry 2014-05, Vol.12 (19), p.3108-3113
Hauptverfasser: Wang, Xiaoe, Xu, Daqian, Miao, Chengxia, Zhang, Qiaohong, Sun, Wei
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Sprache:eng
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Zusammenfassung:A facile and transition-metal-free method was developed through merging the ring opening of benzoxazoles with secondary amines and N-bromosuccinimide (NBS) mediated oxidative cyclization toward the synthesis of 2-aminobenzoxazoles. NBS was selected as a powerful oxidant in the oxidative cyclization of ring-opening amidines to provide the desirable 2-aminobenzoxazoles in excellent yields (up to 94%).
ISSN:1477-0520
1477-0539
DOI:10.1039/c4ob00386a