4.8 Article

Efficient Approach to 4-Sulfonamidoquinolines via Copper(I)-Catalyzed Cascade Reaction of Sulfonyl Azides with Alkynyl Imines

Journal

ORGANIC LETTERS
Volume 15, Issue 7, Pages 1480-1483

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol400219n

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Funding

  1. NSF of China [21202048]
  2. Program for Minjiang Scholar program [10BS216]
  3. Science Research Item of Science and Technology of Xiamen City [3502z201014]
  4. Fundamental Research Funds of Huaqiao University

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A novel and efficient approach to 4-sulfonamidoquinolines via copper-catalyzed cascade reaction of sulfonyl azides with alkynyl imines has been developed in which a 1,3-dipole cycloadditioniketenimine formation/6 pi-electrocyclization/[1,3]-H shift cascade reaction was involved. Various 4-sulfonamidoquinolines were afforded in up to 84% yield for 19 examples. This synthetic strategy features with atom economy, concise steps, easy operation, and mild reaction conditions.

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