4.8 Article

CuX Dual Catalysis: Construction of Oxazolo[2,3-b][1,3]oxazines via a Tandem CuAAC/Ring Cleavage/[4+2+3] Annulation Reaction

Journal

ORGANIC LETTERS
Volume 24, Issue 40, Pages 7300-7304

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c02705

Keywords

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Funding

  1. Applied Basic Research Fund project of Guangdong Province of China [2019A1515110918]
  2. Science and Technology Planning Program of Zhanjiang [2021A05247]
  3. Key Discipline Construction Project of Guangdong Medical University [4SG22004G]
  4. Scientific Research Fund of Hunan Provincial Education Department [21A0613]
  5. Doctoral Research Fund of Hunan University of Medicine [2020122005]

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CuX was used as a simple dual catalyst strategy for the tandem transformations of fused oxazolo[2,3-b][1,3]oxazines. Copper catalyzed the CuAAC/ring cleavage/[4+2] annulation reaction using terminal ynones, sulfonyl azides, and nitriles, while halogen catalyzed the ring cleavage and [2+3] annulation of oxiranes to form the final fused products. This study provides a four-component, one-pot strategy for synthesizing complex fused heterocycles from simple ingredients and expands the application of CuAAC in organic synthesis.
CuX as a simple dual catalyst strategy that promotes the tandem transformations of fused oxazolo[2,3-b][1,3]oxazines has been developed. Copper catalyzed terminal ynones, sulfonyl azides, and nitriles for the CuAAC/ring cleavage/[4+2] annulation reaction, while the halogen catalyzed ring cleavage and [2+3] annulation of oxiranes to form the final fused products. This study provides a four-component, one-pot strategy for synthesizing complex fused heterocycles from simple ingredients and expands the application of CuAAC in organic synthesis.

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