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

J Org Chem

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.

Published: December 2021

AI Article Synopsis

  • A new method has been created to efficiently synthesize polysubstituted oxazol-2(3)-ones using a combination of rearrangement and cyclization reactions.
  • This process uses easily accessible materials and operates under mild conditions, making it simple to execute.
  • The method is notable for its high selectivity, ability to accommodate various functional groups, and it is environmentally friendly as it does not require metals.

Article Abstract

An efficient and straightforward synthesis of polysubstituted oxazol-2(3)-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.

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Source
http://dx.doi.org/10.1021/acs.joc.1c02276DOI Listing

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