Download PDF
Synthesis 2022; 54(02): 429-438
DOI: 10.1055/a-1625-9538
paper

A Catalyst-Free Synthesis of Fused Perfluoroalkylated 2,3-Dihydroisoxazoles via Oxa-Michael-Aldol Annulation

Authors

  • Wei Zhou‡

    a   School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China

  • Lan Yao‡

    b   Inspection Department, Shanghai Blood Center, Shanghai 200051, P. R. of China

  • Yongxiurong Liu

    c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China

  • Lichun Shen

    d   Qianweichang College, Shanghai University, Shanghai, 200444, P. R. of China

  • Jie Chen

    c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China

  • Hongmei Deng

    e   Laboratory for Microstructures, Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China

  • Min Shao

    e   Laboratory for Microstructures, Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China

  • Hui Zhang∗

    c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
    e   Laboratory for Microstructures, Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China

  • Xiaojun Tang∗

    c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China

  • Weiguo Cao∗

    a   School of Environmental and Chemical Engineering, Shanghai University, Shanghai 200444, P. R. of China
    c   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China
    f   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

The authors are grateful to the National Natural Science Foundation of China (Grant No. 21672138) for financial support.
Further Information
   Permissions and Reprints All articles of this category


Graphical Abstract

Preview

Abstract

A novel synthesis of fused perfluoroalkylated 2,3-dihydroisoxazoles is achieved via oxa-Michael-aldol annulation between perfluoroalk-2-ynoates and N-hydroxyimides. This method provides a convenient route for the synthesis of pyrrolidin-2-one-fused perfluoroalkylated 2,3-dihydroisoxazoles in yields of up to 97%. Diverse and pharmaceutically attractive polycyclic scaffolds can be obtained rapidly and efficiently under these mild, catalyst-free conditions.

Key words

dihydroisoxazoles - piperidin-2-ones - perfluoroalkylated - oxa-Michael-aldol annulation - catalyst-free conditions

Supporting Information



Publication History

Received: 03 August 2021

Accepted after revision: 31 August 2021

Accepted Manuscript online:
31 August 2021

Article published online:
17 September 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany