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