4.6 Article

Visible-Light-Mediated Aerobic Tandem Dehydrogenative Povarov/Aromatization Reaction: Synthesis of Isocryptolepines

期刊

CHEMISTRY-A EUROPEAN JOURNAL
卷 26, 期 1, 页码 269-274

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201903921

关键词

aerobic oxidation; cycloaddition; dehydrogenation; heterocycles; photochemistry

资金

  1. University of Rostock - German Academic Exchange Service (DAAD) [57315854]
  2. Vietnam National University-Hanoi University of Science - German Academic Exchange Service (DAAD) [57315854]
  3. Federal Ministry for Economic Cooperation and Development (BMZ)
  4. University of Rostock

向作者/读者索取更多资源

A metal-free, photoinduced aerobic tandem amine dehydrogenation/Povarov cyclization/aromatization reaction between N-aryl glycine esters and indoles leads to tetracyclic 11H-indolo[3,2-c]quinolines under mild conditions and with high yields. The reaction can be performed by using molecular iodine along with visible light, or by combining an organic photoredox catalyst with a halide anion. Mechanistic studies reveal that product formation occurs through a combination of radical-mediated oxidation steps with an iminium ion or N-haloiminium ion [4+2]-cycloaddition, and the N-heterocyclic products constitute new analogues of the antiplasmodial natural alkaloid isocryptolepine.

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