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

Zhiming Wang; Xingzhu Xu; Zhanshou Gu; Wei Feng; Houjun Qian; Zhengyi Li; Xiaoqiang Sun; Ohyun Kwon

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,*^a Xingzhu Xu,^a Zhanshou Gu,^a Wei Feng,^a Houjun Qian,^a Zhengyi Li,^a Xiaoqiang Sun^a and Ohyun Kwon*^b

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* Corresponding authors

^a Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, P. R. China
E-mail: zhiming@cczu.edu.cn

^b Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, USA
E-mail: ohyun@chem.ucla.edu

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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Publication details

The article was received on 24 Oct 2015, accepted on 23 Dec 2015 and first published on 24 Dec 2015

Article type: Communication

DOI: 10.1039/C5CC08596A

Author version available: Download Author version (PDF)

Citation: Chem. Commun., 2016,52, 2811-2814

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

Z. Wang, X. Xu, Z. Gu, W. Feng, H. Qian, Z. Li, X. Sun and O. Kwon, Chem. Commun., 2016, 52, 2811
DOI: 10.1039/C5CC08596A
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Chemical Communications

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

Abstract

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

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