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

10 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 1837193: Experimental Crystal Structure Determination
Bandi, V. (Creator), Kavala, V. (Creator), Konala, A. (Creator), Hsu, C. (Creator), Villuri, B. K. (Creator), Reddy, S. R. (Creator), Lin, L. (Creator), Kuo, C. (Creator) & Yao, C. (Creator), Unknown Publisher, 2019
DOI: 10.5517/ccdc.csd.cc1znr9p, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1znr9p&sid=DataCite
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CCDC 1904123: Experimental Crystal Structure Determination
Bandi, V. (Creator), Kavala, V. (Creator), Konala, A. (Creator), Hsu, C. (Creator), Villuri, B. K. (Creator), Reddy, S. R. (Creator), Lin, L. (Creator), Kuo, C. (Creator) & Yao, C. (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
CCDC 1904121: Experimental Crystal Structure Determination
Bandi, V. (Creator), Kavala, V. (Creator), Konala, A. (Creator), Hsu, C. (Creator), Villuri, B. K. (Creator), Reddy, S. R. (Creator), Lin, L. (Creator), Kuo, C. (Creator) & Yao, C. (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

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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.",

author = "Vijayalakshmi Bandi and Veerababurao Kavala and Ashok Konala and Hsu, {Che Hao} and Villuri, {Bharath Kumar} and Reddy, {Sabbasani Rajasekhara} and Lichun Lin and Kuo, {Chun Wei} and Yao, {Ching Fa}",

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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

AU - Kuo, Chun Wei

AU - Yao, Ching Fa

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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 1837193: Experimental Crystal Structure Determination

CCDC 1904123: Experimental Crystal Structure Determination

CCDC 1904121: Experimental Crystal Structure Determination

Cite this