4.7 Article

Metal-Free Oxidative Spirocyclization of Alkynes with Sulfonylhydrazides Leading to 3-Sulfonated Azaspiro[4,5]trienones

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 80, Issue 10, Pages 4966-4972

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.5b00361

Keywords

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Funding

  1. National Natural Science Foundation of China [21302109, 21302110, 21375075]
  2. Taishan Scholar Foundation of Shangdong Province
  3. Excellent Middle-Aged and Young Scientist Award Foundation of Shangdong Province [BS2013YY019]
  4. Scientific Research Foundation of Qufu Normal University [BSQD 2012020]

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A novel and direct oxidative spirocyclization of arylpropiolamides with sulfonylhydrazides leading to 3-sulfonated azaspiro[4,5]trienones has been developed under metal-free conditions. The reaction is performed in a tandem: manner constituted by the sequential sulfonylation of alkynes, ipso-carbocyclization, dearomatization, hydration, and oxidation processes, providing a convenient and efficient approach to Various sulfonated,azaspiro[4,5] trienones of biological importance.

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