4.7 Article

Metal-Free [2+2+2] Cycloaddition of Ynamide-Nitriles with Ynamides: A Highly Regio- and Chemoselective Synthesis of δ-Carboline Derivatives

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 21, Pages 13308-13324

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b02112

Keywords

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Funding

  1. National Natural Science Foundation of China [21572154, 21772181, 81803344]
  2. NSFC-Shandong Joint Fund for Marine Science Research Centers [U1606403]
  3. Key R&D Project of Shandong Province [2018GSF118022]
  4. Fundamental Research Funds for the Central Universities [201612013]
  5. Qingdao Scientific and Technological Innovation Center for Marine Biomedicine Development Grant [2017-CXZX01-1-1]

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A metal-free formal [2 + 2 + 2] cycloaddition of functionalized ynamide-nitriles with ynamides is disclosed which offers highly efficient access to polysubstituted delta-carboline derivatives under the mediation of TfOH. This strategy is highly regioselective and chemoselective and displays mild conditions, high yields, and efficiency (within 1 min) in addition to substrates scopes (56 examples).

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