Synthesis of Polysubstituted Cyclopentene and Cyclopenta[ b]carbazole Analogues from Unsymmetrical 4-Arylidene-3,6-diarylhex-2-en-5-ynal and Indole Derivatives via an Iodine Mediated Electrocyclization Reaction

Vijayalakshmi Bandi; Veerababurao Kavala; Ashok Konala; Che Hao Hsu; Bharath Kumar Villuri; Sabbasani Rajasekhara Reddy; Lichun Lin; Chun Wei Kuo; Ching Fa Yao

doi:10.1021/acs.joc.8b02168

Synthesis of Polysubstituted Cyclopentene and Cyclopenta[ b]carbazole Analogues from Unsymmetrical 4-Arylidene-3,6-diarylhex-2-en-5-ynal and Indole Derivatives via an Iodine Mediated Electrocyclization Reaction

Vijayalakshmi Bandi
, Veerababurao Kavala
, Ashok Konala
, Che Hao Hsu
, Bharath Kumar Villuri
, Sabbasani Rajasekhara Reddy
, Lichun Lin
, Chun Wei Kuo
, Ching Fa Yao^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

12 Citations (Scopus)

Abstract

An efficient method for the synthesis of polysubstituted cyclopentene and cyclopenta[b]carbazole derivatives through the iodine-promoted electrocyclization of substituted indoles and 4-arylidene-3,6-diarylhex-2-en-5-ynal derivatives is reported. Polysubstituted cyclopentene derivatives were produced through 4π electrocyclization reactions with indole, 7-methylindole, and 5-bromoindole as coupling partners, whereas cyclopenta[b]carbazole derivatives were produced via 6π electrocyclization in the case of methoxy (-OMe)-substituted indoles. The methods reported herein diastereo- and regioselectively proceed under straightforward and mild conditions.

Original language	English
Pages (from-to)	3036-3044
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	84
Issue number	6
DOIs	https://doi.org/10.1021/acs.joc.8b02168
Publication status	Published - 2019 Mar 15

ASJC Scopus subject areas

Organic Chemistry

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CCDC 1837195: Experimental Crystal Structure Determination
Bandi, V. (Creator), Kavala, V. (Creator), Konala, A. (Creator), Hsu, C.-H. (Creator), Villuri, B. K. (Creator), Reddy, S. R. (Creator), Lin, L. (Creator), Kuo, C.-W. (Creator) & Yao, C.-F. (Creator), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1znrcr, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1znrcr&sid=DataCite
Dataset
CCDC 1904121: Experimental Crystal Structure Determination
Bandi, V. (Creator), Kavala, V. (Creator), Konala, A. (Creator), Hsu, C.-H. (Creator), Villuri, B. K. (Creator), Reddy, S. R. (Creator), Lin, L. (Creator), Kuo, C.-W. (Creator) & Yao, C.-F. (Creator), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc21xd8n, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc21xd8n&sid=DataCite
Dataset
CCDC 1904123: Experimental Crystal Structure Determination
Bandi, V. (Creator), Kavala, V. (Creator), Konala, A. (Creator), Hsu, C.-H. (Creator), Villuri, B. K. (Creator), Reddy, S. R. (Creator), Lin, L. (Creator), Kuo, C.-W. (Creator) & Yao, C.-F. (Creator), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc21xdbq, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc21xdbq&sid=DataCite
Dataset

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Bandi, V., Kavala, V., Konala, A., Hsu, C. H., Villuri, B. K., Reddy, S. R., Lin, L., Kuo, C. W., & Yao, C. F. (2019). Synthesis of Polysubstituted Cyclopentene and Cyclopenta[ b]carbazole Analogues from Unsymmetrical 4-Arylidene-3,6-diarylhex-2-en-5-ynal and Indole Derivatives via an Iodine Mediated Electrocyclization Reaction. Journal of Organic Chemistry, 84(6), 3036-3044. https://doi.org/10.1021/acs.joc.8b02168

Synthesis of Polysubstituted Cyclopentene and Cyclopenta[ b]carbazole Analogues from Unsymmetrical 4-Arylidene-3,6-diarylhex-2-en-5-ynal and Indole Derivatives via an Iodine Mediated Electrocyclization Reaction. / Bandi, Vijayalakshmi; Kavala, Veerababurao; Konala, Ashok et al.
In: Journal of Organic Chemistry, Vol. 84, No. 6, 15.03.2019, p. 3036-3044.

Research output: Contribution to journal › Article › peer-review

Bandi, V, Kavala, V, Konala, A, Hsu, CH, Villuri, BK, Reddy, SR, Lin, L, Kuo, CW & Yao, CF 2019, 'Synthesis of Polysubstituted Cyclopentene and Cyclopenta[ b]carbazole Analogues from Unsymmetrical 4-Arylidene-3,6-diarylhex-2-en-5-ynal and Indole Derivatives via an Iodine Mediated Electrocyclization Reaction', Journal of Organic Chemistry, vol. 84, no. 6, pp. 3036-3044. https://doi.org/10.1021/acs.joc.8b02168

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title = "Synthesis of Polysubstituted Cyclopentene and Cyclopenta[ b]carbazole Analogues from Unsymmetrical 4-Arylidene-3,6-diarylhex-2-en-5-ynal and Indole Derivatives via an Iodine Mediated Electrocyclization Reaction",

abstract = "An efficient method for the synthesis of polysubstituted cyclopentene and cyclopenta[b]carbazole derivatives through the iodine-promoted electrocyclization of substituted indoles and 4-arylidene-3,6-diarylhex-2-en-5-ynal derivatives is reported. Polysubstituted cyclopentene derivatives were produced through 4π electrocyclization reactions with indole, 7-methylindole, and 5-bromoindole as coupling partners, whereas cyclopenta[b]carbazole derivatives were produced via 6π electrocyclization in the case of methoxy (-OMe)-substituted indoles. The methods reported herein diastereo- and regioselectively proceed under straightforward and mild conditions.",

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AU - Bandi, Vijayalakshmi

AU - Kavala, Veerababurao

AU - Konala, Ashok

AU - Hsu, Che Hao

AU - Villuri, Bharath Kumar

AU - Reddy, Sabbasani Rajasekhara

AU - Lin, Lichun

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AB - An efficient method for the synthesis of polysubstituted cyclopentene and cyclopenta[b]carbazole derivatives through the iodine-promoted electrocyclization of substituted indoles and 4-arylidene-3,6-diarylhex-2-en-5-ynal derivatives is reported. Polysubstituted cyclopentene derivatives were produced through 4π electrocyclization reactions with indole, 7-methylindole, and 5-bromoindole as coupling partners, whereas cyclopenta[b]carbazole derivatives were produced via 6π electrocyclization in the case of methoxy (-OMe)-substituted indoles. The methods reported herein diastereo- and regioselectively proceed under straightforward and mild conditions.

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Synthesis of Polysubstituted Cyclopentene and Cyclopenta[ b]carbazole Analogues from Unsymmetrical 4-Arylidene-3,6-diarylhex-2-en-5-ynal and Indole Derivatives via an Iodine Mediated Electrocyclization Reaction

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1837195: Experimental Crystal Structure Determination

CCDC 1904121: Experimental Crystal Structure Determination

CCDC 1904123: Experimental Crystal Structure Determination

Cite this