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Discovery of cationic domino reaction under the NMR experiment conditions: diastereoselective dimerization of 2-arylmethylideneindolin-3-ones to pentacyclic 3-hydroxyindolenine system

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Abstract

NMR spectroscopy (1D and 2D) showed that the protonation of the capto-dative heterocyclic α-amino enones, viz., (Z)-2-arylmethylideneindolin-3-ones, with strong acids led to stable (aryl)(3-hydroxyindol-2-yl)methyl cations. These substrates in trifluoroacetic acid underwent cationic domino reaction, which resulted in polynuclear pyrido[1,2-a: 5,6-b′]-[1,2′]biindoles.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    A. S. Peregudov, I. A. Godovikov, I. N. Fedorova, O. V. Istomina, K. A. Lyssenko & V. S. Velezheva

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  1. A. S. Peregudov
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  2. I. A. Godovikov
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  3. I. N. Fedorova
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  4. O. V. Istomina
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  5. K. A. Lyssenko
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  6. V. S. Velezheva
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Correspondence to A. S. Peregudov.

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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya on the occasion of her anniversary.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0849–0853, March, 2013.

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Peregudov, A.S., Godovikov, I.A., Fedorova, I.N. et al. Discovery of cationic domino reaction under the NMR experiment conditions: diastereoselective dimerization of 2-arylmethylideneindolin-3-ones to pentacyclic 3-hydroxyindolenine system. Russ Chem Bull 62, 850–854 (2013). https://doi.org/10.1007/s11172-013-0116-z

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  • DOI: https://doi.org/10.1007/s11172-013-0116-z

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