4.7 Article

Oxidative Cyclization of β-Aminoacrylamides Mediated by PhIO: Chemoselective Synthesis of Isoxazoles and 2H-Azirines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 24, Pages 14999-15008

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02132

Keywords

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Funding

  1. National Natural Science Foundation of China [21502185, 21542006]
  2. Department of Science and Technology of Jilin Province [20170203005SF]
  3. CAS President's International Fellowship for Postdoctoral Researchers [2016PT021]
  4. Youth Innovation Promotion Association CAS [2018261]

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Cyclization of a variety of beta-aminoacrylamides in the presence of iodosobenzene (PhIO) is described. This process features mild reaction conditions, simple execution, and high chemoselectivity and thereby provides an efficient protocol for the divergent synthesis of substituted isoxazoles and 2H-azirines via switchable N-O and N-C bond formation controlled by simply varying the beta-substituent R-3 of the readily available substrates.

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