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. 2016 Feb 14;52(13):2811-4.
doi: 10.1039/c5cc08596a.

Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4'-quinoline]s

Zhiming Wang  1 , Xingzhu Xu  1 , Zhanshou Gu  1 , Wei Feng  1 , Houjun Qian  1 , Zhengyi Li  1 , Xiaoqiang Sun  1 , Ohyun Kwon  2
Affiliations

Nazarov cyclization of 1,4-pentadien-3-ols: preparation of cyclopenta[b]indoles and spiro[indene-1,4'-quinoline]s

Zhiming Wang et al. Chem Commun (Camb). .

Abstract

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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Figures

Scheme 1
Scheme 1
Intramolecular interrupted Nazarov cyclization of 1,4-pentadien-3-ols.
Scheme 2
Scheme 2
Nazarov cyclizations of polysubstituted 1,4-pentadien-3-ols.
Scheme 3
Scheme 3
Synthesis of spiro[indene-1,4′-quinoline]s.
Scheme 4
Scheme 4
Mechanistic studies.
See this image and copyright information in PMC

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