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Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[ b ]indoles and spiro[indene-1,4′-quinoline]s
- Wang, Zhiming;
- Xu, Xingzhu;
- Gu, Zhanshou;
- Feng, Wei;
- Qian, Houjun;
- Li, Zhengyi;
- Sun, Xiaoqiang;
- Kwon, Ohyun
Published Web Location
https://doi.org/10.1039/c5cc08596aAbstract
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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