4.7 Article

Gold-Catalyzed Cyclization of 3-(2′-Azidoaryl)-1-arylpropargyl Carbonates or 3-Aryl-1-(2′-azidoaryl)propargyl Carbonates to Produce Quinolines

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 78, Issue 18, Pages 9120-9126

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jo401324k

Keywords

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Funding

  1. National Natural Science Foundation of China [20872127, J0830431]
  2. National Basic Research Program of China (973 Program) [2009CB825300]
  3. CAS Academician Foundation of Zhejiang Province
  4. Fundamental Research Funds for the Central Universities

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A gold-catalyzed cyclization of 3-(2'-azidoaryl)-1-arylpropargyl carbonates to generate substituted quinolines via a sequence of 3,3-rearrangement, 6-endo-trig cyclization and denitrogenation has been developed. Similar products could be obtained from 3-aryl-1-(2'-azidoaryl)propargyl carbonates under different gold catalytic conditions via a sequential 6-endo-dig cyclization, denitrogenation, and 1,2-H shift process.

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