Benzannulation of 2-Alkenylindoles using Aldehydes by Sequential Triple-Relay Catalysis: A Route to Carbazoles and Carbazole Alkaloids

被引:52
作者
Banerjee, Ankush [1 ]
Sahu, Samrat [1 ]
Maji, Modhu Sudan [1 ]
机构
[1] Indian Inst Technol Kharagpur, Dept Chem, Kharagpur 721302, W Bengal, India
关键词
alkaloids; annulation; carbazoles; conjugated materials; sequential catalysis; METAL-DIENE COMPLEXES; C-H FUNCTIONALIZATION; 1ST TOTAL-SYNTHESIS; MEDIATED TOTAL-SYNTHESIS; ORGANIC-SYNTHESIS; BISCARBAZOLE ALKALOIDS; SUBSTITUTED CARBAZOLES; BOND AMINATION; HOST MATERIALS; INDOLES;
D O I
10.1002/adsc.201700092
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Benzannulation of 2-alkenylindoles with readily available aldehydes, under one-pot sequential triple-relay-catalysis, provides an easy access to several structurally unique carbazoles including 2-and 3-alkenylcarbazoles. This protecting group-free method enabled one-pot synthesis of alkaloids such as hyellazole and 6-chlorohyellazole, and the formal syntheses of seven other alkaloids. Construction of the core structure, present in murastifoline A, murrafoline E, and related alkaloids was also demonstrated. Even conjugated 3,3'-biscarbazoles can also be synthesized by one-pot, two-fold sequential triple-relay catalysis.
引用
收藏
页码:1860 / 1866
页数:7
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