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

doi:10.1039/c5cc08596a

. 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 Wang¹, Xingzhu Xu¹, Zhanshou Gu¹, Wei Feng¹, Houjun Qian¹, Zhengyi Li¹, Xiaoqiang Sun¹, Ohyun Kwon²

Affiliations

¹ Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. China. zhiming@cczu.edu.cn.
² Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569, USA. ohyun@chem.ucla.edu.

PMID: 26771024
PMCID: PMC5560599
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 et al. Chem Commun (Camb). 2016.

. 2016 Feb 14;52(13):2811-4.

doi: 10.1039/c5cc08596a.

Authors

Zhiming Wang¹, Xingzhu Xu¹, Zhanshou Gu¹, Wei Feng¹, Houjun Qian¹, Zhengyi Li¹, Xiaoqiang Sun¹, Ohyun Kwon²

Affiliations

¹ Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, Jiangsu 213164, P. R. China. zhiming@cczu.edu.cn.
² Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, CA 90095-1569, USA. ohyun@chem.ucla.edu.

PMID: 26771024
PMCID: PMC5560599
DOI: 10.1039/c5cc08596a

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**
Intramolecular interrupted Nazarov cyclization of 1,4-pentadien-3-ols.

**Scheme 2**
Nazarov cyclizations of polysubstituted 1,4-pentadien-3-ols.

**Scheme 3**
Synthesis of spiro[indene-1,4′-quinoline]s.

See this image and copyright information in PMC

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References

1. For recent selected reviews on indoles, see:
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[1] For recent selected reviews on indoles, see:

Lancianesi S, Palmieri A, Petrini M. Chem Rev. 2014;114:7108. - PubMed

Kochanowska-Karamyan AJ, Hamann MT. Chem Rev. 2010;110:4489. - PMC - PubMed

Sharma V, Kumar P, Pathak D. J Heterocycl Chem. 2010;47:491.

[2] For recent selected reviews on indoles, see:

[3] Lancianesi S, Palmieri A, Petrini M. Chem Rev. 2014;114:7108. - PubMed

[4] Kochanowska-Karamyan AJ, Hamann MT. Chem Rev. 2010;110:4489. - PMC - PubMed

[5] Sharma V, Kumar P, Pathak D. J Heterocycl Chem. 2010;47:491.

[6] Kong YC, Cheng KF, Cambie RC, Waterman PG. J Chem Soc, Chem Commun. 1985;47

[7] Kong YC, Cheng KF, Cambie RC, Waterman PG. J Chem Soc, Chem Commun. 1985;47

[8] Stratmann K, Moore RE, Bonjouklian R, Deeter JB, Patterson GML, Shaffer S, Smith CD, Smitka TA. J Am Chem Soc. 1994;116:9935.

[9] Stratmann K, Moore RE, Bonjouklian R, Deeter JB, Patterson GML, Shaffer S, Smith CD, Smitka TA. J Am Chem Soc. 1994;116:9935.

[10] Nakazawa J, Yajima J, Usui T, Ueki M, Takatsuki A, Imoto M, Toyoshima YY, Osada H. Chem Biol. 2005;10:131. - PubMed

[11] Nakazawa J, Yajima J, Usui T, Ueki M, Takatsuki A, Imoto M, Toyoshima YY, Osada H. Chem Biol. 2005;10:131. - PubMed

[12] Jordan JA, Gribble GW, Badenock JC. Tetrahedron Lett. 2011;52:6772.

[13] Jordan JA, Gribble GW, Badenock JC. Tetrahedron Lett. 2011;52:6772.

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

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