Organic Chemistry

Syntheses of Hydrocarbazole Derivatives via Brønsted acid-Initiated Diels-Alder Cycloaddition/retro-Michael Addition Cascade Reaction of Azepino[4,5-b]indoles and Acrolein

Authors

  • Fukai Xie Shenyang Pharmaceutical University ,
  • Xiang Li Shenyang Pharmaceutical University ,
  • Liangyu Xu Shenyang Pharmaceutical University ,
  • Jun Ma Shenyang Pharmaceutical University ,
  • Lei Sun Shenyang Pharmaceutical University ,
  • Bo Zhang Shenyang Pharmaceutical University ,
  • Bin Lin Shenyang Pharmaceutical University ,
  • Maosheng Cheng Shenyang Pharmaceutical University ,
  • Yongxiang Liu Shenyang Pharmaceutical University

Abstract

A unique approach to hydrocarbazoles bearing an all-carbon quaternary center at C4a position was developed via a Brønsted acid-initiated Diels-Alder cycloaddition/retro-Michael addition cascade process from facilely prepared azepino[4,5-b]indoles and commercially available acrolein. The method provided a range of hydrocarbazoles in good to excellent yields. The practi-cality of this transformation was demonstrated by scale-up experiment and various transformations to several hydrocarbazole derivatives.

Content

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Supplementary material

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Syntheses of Hydrocarbazole Derivatives via Brønsted acid-Initiated Diels-Alder Cycloaddition/retro-Michael Addition Cascade Reaction of Azepino[4,5-b]indoles and Acrolein
The supporting information of the paper entitled 'Syntheses of Hydrocarbazole Derivatives via Brønsted acid-Initiated Diels-Alder Cycloaddition/retro-Michael Addition Cascade Reaction of Azepino[4,5-b]indoles and Acrolein'