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

Research output: Contribution to journalArticle

1 Citation (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 languageEnglish
Pages (from-to)3036-3044
Number of pages9
JournalJournal of Organic Chemistry
Volume84
Issue number6
DOIs
Publication statusPublished - 2019 Mar 15

Fingerprint

Indoles
Cyclopentanes
Iodine
Derivatives
indole
carbazole
7-methylindole

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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; Hsu, Che Hao; Villuri, Bharath Kumar; Reddy, Sabbasani Rajasekhara; Lin, Lichun; Kuo, Chun Wei; Yao, Ching Fa.

In: Journal of Organic Chemistry, Vol. 84, No. 6, 15.03.2019, p. 3036-3044.

Research output: Contribution to journalArticle

Bandi, Vijayalakshmi ; Kavala, Veerababurao ; Konala, Ashok ; Hsu, Che Hao ; Villuri, Bharath Kumar ; Reddy, Sabbasani Rajasekhara ; Lin, Lichun ; Kuo, Chun Wei ; Yao, Ching Fa. / 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. In: Journal of Organic Chemistry. 2019 ; Vol. 84, No. 6. pp. 3036-3044.
@article{f6b4ad4d7a4343e6ab042ceb54aa4d95,
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}",
year = "2019",
month = "3",
day = "15",
doi = "10.1021/acs.joc.8b02168",
language = "English",
volume = "84",
pages = "3036--3044",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "6",

}

TY - JOUR

T1 - 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

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

PY - 2019/3/15

Y1 - 2019/3/15

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=85055640907&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=85055640907&partnerID=8YFLogxK

U2 - 10.1021/acs.joc.8b02168

DO - 10.1021/acs.joc.8b02168

M3 - Article

C2 - 30359006

AN - SCOPUS:85055640907

VL - 84

SP - 3036

EP - 3044

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 6

ER -