Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4′-quinoline]s
2016
Wang, Zhiming | Xu, Xingzhu | Gu, Zhanshou | Feng, Wei | Qian, Houjun | Li, Zhengyi | Sun, Xiaoqiang | Kwon, Ohyun
The first Lewis acid-catalyzed intramolecular interrupted Nazarov cyclization of 1,4-pentadien-3-ols is described. Using FeBr₃ as the catalyst, a series of new substituted cyclopenta[b]indoles was prepared—through a sequence of Nazarov cyclization, nucleophilic amination, and isomerization—with good yields and high diastereo- and regioselectivities. A similar catalytic process was also developed for the synthesis of structurally interesting spiro[indene-1,4′-quinoline]s.
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