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α-Indolyl-β-nitroacrylates. Synthesis and structure

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Abstract

A one-pot procedure has been developed for the synthesis of α-indolyl-β-nitroacrylates by reaction of β-bromo-β-nitroacrilates with indole and substituted indoles. All indolylnitroacrilates thus obtained have Z configuration of the double bond. According to the X-ray diffraction data, ethyl 2-(1-methyl-1H-indol-3-yl)-3-nitroacrylate is characterized by s-trans conformation of the double C=C bond and indole ring; its crystal packing involves intermolecular hydrogen bonds C-H…O and C-H…π with formation of centrosymmetric dimers which give rise to bilayer supramolecular structures.

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Authors and Affiliations

  1. Hertzen Russian State Pedagogical University, nab. r. Moiki 48, St. Petersburg, 191186, Russia

    V. M. Berestovitskaya, S. V. Makarenko, A. S. Smirnov, A. I. Pekki & Z. M. Sarkisyan

  2. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center, Russian Academy of Sciences, ul. Arbuzova 8, Kazan, 420088, Tatarstan, Russia

    A. T. Gubaidullin & I. A. Litvinov

Authors
  1. V. M. Berestovitskaya
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  2. S. V. Makarenko
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  3. A. S. Smirnov
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  4. A. T. Gubaidullin
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  5. I. A. Litvinov
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  6. A. I. Pekki
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  7. Z. M. Sarkisyan
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Correspondence to V. M. Berestovitskaya.

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Original Russian Text © V.M. Berestovitskaya, S.V. Makarenko, A.S. Smirnov, A.T. Gubaidullin, I.A. Litvinov, A.I. Pekki, Z. M. Sarkisyan, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 5, pp. 820–827.

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Berestovitskaya, V.M., Makarenko, S.V., Smirnov, A.S. et al. α-Indolyl-β-nitroacrylates. Synthesis and structure. Russ J Gen Chem 78, 963–970 (2008). https://doi.org/10.1134/S1070363208050228

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  • DOI: https://doi.org/10.1134/S1070363208050228

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