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

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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
Issue number6
Publication statusPublished - 2019 Mar 15


ASJC Scopus subject areas

  • Organic Chemistry

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