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

Baibin Li; Jingwen Yuan; Xuebei Ye; Rui Zhang; Jiacheng Li; Yu Wang; Jiana Hu; Dewen Dong

doi:10.1021/acs.joc.1c02276

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

J Org Chem. 2021 Dec 17;86(24):17944-17954. doi: 10.1021/acs.joc.1c02276. Epub 2021 Dec 6.

Authors

Baibin Li^{1

2}, Jingwen Yuan¹, Xuebei Ye^{1

2}, Rui Zhang¹, Jiacheng Li^{1

2}, Yu Wang^{1

2}, Jiana Hu^{1

2}, Dewen Dong^{1

2}

Affiliations

¹ CAS Key Laboratory of High-Performance Synthetic Rubber and Its Composite Materials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China.
² University of Science and Technology of China, Hefei 230026, P. R. China.

PMID: 34872249
DOI: 10.1021/acs.joc.1c02276

Abstract

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.