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Diastereoselective construction of carbazole-based spirooxindoles via the Levy three-component reaction

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Abstract

The CuSO4 catalyzed three-component reaction of indole-2-acetate, aromatic aldehydes and 3-methyleneoxindoles in toluene at 130 °C afforded polysubstituted spiro[carbazole-3,3′-indolines] in good yields and with high diastereoselectivity. When isatylidene malononitriles were used as dienophiles, regio-isomeric spiro[carbazole-2,3′-indolines] were selectively obtained. A similar three-component reaction with 2-arylidene-1,3-indanediones resulted in polysubstituted spiro[carbazole-3,2′-indenes] in satisfactory yields and with high diastereoselectivity. The stereochemistry of the diastereoisomers of the spiro compounds was clearly elucidated by analysis of NMR spectra and determination of fourteen single crystal structures. The reaction mechanism included formation of reactive 2,3-dimethyleneindoline and a sequential Diels–Alder reaction.

Graphical abstract: Diastereoselective construction of carbazole-based spirooxindoles via the Levy three-component reaction

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Publication details

The article was received on 15 Sep 2019, accepted on 02 Dec 2019 and first published on 02 Dec 2019


Article type: Paper
DOI: 10.1039/C9OB02013F
Org. Biomol. Chem., 2020, Advance Article

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    Diastereoselective construction of carbazole-based spirooxindoles via the Levy three-component reaction

    S. Zhan, J. Sun, R. Liu and C. Yan, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/C9OB02013F

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