4.6 Article

Copper-catalyzed three-component reaction to synthesize polysubstituted imidazo[1,2-a]pyridines

Journal

RSC ADVANCES
Volume 12, Issue 31, Pages 20199-20205

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2ra02722d

Keywords

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Funding

  1. Foundation and Applied Basic Research Fund project of Guangdong Province of China [2019A1515110918]
  2. Science and Technology Planning Program of Zhanjiang [2021A05247]
  3. Medical Scientific Research Foundation of Guangdong Province [A2021037, A2020202]
  4. Key Discipline Construction Project of Guangdong Medical University [4SG22004G]
  5. Innovation and Entrepreneurship Team Leads the Pilot Program of Zhanjiang [2020LHJH005]
  6. Science and technology program of Guangdong Province [2019B090905011]

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An efficient and simple three-component cascade reaction was reported, providing a variety of polysubstituted imidazo[1,2-a]pyridine derivatives in moderate to excellent yields. The reaction proceeds through a CuAAC/ring-cleavage process and forms a highly active intermediate alpha-acyl-N-sulfonyl ketenimine without the need for a base.
An efficient three-component one-pot and operationally simple cascade of 2-aminopyridines with sulfonyl azides and terminal ynones is reported, providing a variety of polysubstituted imidazo[1,2-a]pyridine derivatives in moderate to excellent yields. In particular, the reaction goes a through CuAAC/ring-cleavage process and forms a highly active intermediate alpha-acyl-N-sulfonyl ketenimine with base free.

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