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Selective synthesis of oxazoles and pyrazines from α-bromo-1-phenylethanone using a by-product-promoted strategy

Author:
Liu, Changhui, Zhao, Jiateng, Qiao, Yu, Huang, Wenbo, Rao, Zhonghao, Gu, Yanlong
Source:
Tetrahedron 2018 v.74 no.51 pp. 7351-7357
ISSN:
0040-4020
Subject:
ammonium acetate, chemical reactions, chemical structure, chemoselectivity, drugs, hydrobromic acid, oxazoles, pyrazines
Abstract:
Oxazoles and pyrazines are fundamental heterocycles that widely found in natural products or drugs. In this work, a selective strategy for oxazoles and pyrazines synthesis using α-bromo-1-phenylethanone and ammonium acetate as starting materials was reported. This methodology features mild reaction conditions, readily accessible starting materials and good chemoselectivity. Mechanistic study indicates that this reaction involves a by-product-promoted (BPP) process for the formation of oxazole, that is, the in-situ formed hydrogen bromide (HBr) during the reaction promotes the whole tandem process.
Agid:
6232085