4.7 Article

Gold-Catalyzed Radical-Involved Intramolecular Cyclization of Internal N-Propargylamides for the Construction of 5-Oxazole Ketones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 1, Pages 401-408

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02334

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Funding

  1. National Natural Science Foundation [21772046]
  2. Program of Innovative Research Team of Huaqiao University [Z14 X 0047]
  3. Recruitment Program of Global Experts (1000 Talents Plan)
  4. Natural Science Foundation of Fujian Province [2016J01064]
  5. Huaqiao University

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An expedient strategy for the synthesis of 5-oxazole ketones was developed via homogeneous gold catalysis with 4-MeO-TEMPO as an oxidant. The desired 5-oxazole ketones were achieved in decent yields with an excellent functional group compatibility under mild conditions. The current protocol also represents the first example for merging a gold catalyst and radical chemistry in one-pot synthesis with internal N-propargylamides.

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