PIFA-Mediated Tandem Hofmann-Type Rearrangement and Cyclization Reaction of α‑Acyl-β-aminoacrylamides: Access to Polysubstituted Oxazol-2(3H)‑ones

An efficient and straightforward synthesis of polysubstituted oxazol-2­(3H)-ones has been developed via a tandem Hofmann-type rearrangement and cyclization reaction of various α-acyl-β-aminoacrylamides mediated by phenyl iodine­(III) bis­(trifluoroacetate) (PIFA) in the presence of trifloroacetic ac...

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Bibliographic Details
Published in:Journal of organic chemistry 2021-12, Vol.86 (24), p.17944-17954
Main Authors: Li, Baibin, Yuan, Jingwen, Ye, Xuebei, Zhang, Rui, Li, Jiacheng, Wang, Yu, Hu, Jiana, Dong, Dewen
Format: Article
Language:English
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Summary:An efficient and straightforward synthesis of polysubstituted oxazol-2­(3H)-ones has been developed via a tandem Hofmann-type rearrangement and cyclization reaction of various α-acyl-β-aminoacrylamides mediated by phenyl iodine­(III) bis­(trifluoroacetate) (PIFA) in the presence of trifloroacetic acid (TFA). This novel protocol features readily available starting materials, mild reaction conditions, simple execution, high chemoselectivity, good functional group tolerance, and a metal-free oxidation process.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c02276