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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

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posted on 25.10.2018 by Vijayalakshmi Bandi, Veerababurao Kavala, Ashok Konala, Che-Hao Hsu, Bharath Kumar Villuri, Sabbasani Rajasekhara Reddy, LiChun Lin, Chun-Wei Kuo, Ching-Fa Yao
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.