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Heterocyclization of 2-Nitrobenzoyl-1,1,3,3-tetracyanopropenides under the Action of Hydrogen Chloride in Alcohol

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Abstract

The reaction of 2-[3(4)-nitrobenzoyl]-1,1,3,3-tetracyanopropenides with hydrogen chloride in alcohols leads to the corresponding 4-amino-1-alkoxy-1-[3(4)-nitrophenyl]-3-oxo-6-chloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitrilam through the intermediate formation of 2-{2-hydroxy-2-[3(4)-nitrophenyl]-4-cyano-5-alkoxy-1,2-dihydro-3H-pyrrole-3-ylidene}malononitriles, which can be isolated in low yields. The reaction in an aqueous-alcoholic medium resulted in the preparation of 4-amino-1-hydroxy-1-[3(4)-nitrophenyl]-3-oxo-6-chloro-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles.

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ACKNOWLEDGMENTS

X-ray diffraction studies were performed using the equipment purchased from the budget the Development Program of the Lomonosov Moscow State University.

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Authors and Affiliations

  1. Ulʼyanov Chuvash State University, 428015, Cheboksary, Russia

    Ya. S. Kayukov, A. A. Grigor’ev & S. V. Karpov

  2. Chuvash State Agrarian University, 428003, Cheboksary, Russia

    O. V. Kayukova

  3. Lomonosov Moscow State University, 119991, Moscow, Russia

    V. A. Tafeenko

Authors
  1. Ya. S. Kayukov
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  2. A. A. Grigor’ev
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  3. S. V. Karpov
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  4. O. V. Kayukova
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  5. V. A. Tafeenko
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Corresponding author

Correspondence to Ya. S. Kayukov.

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Additional information

Translated from Zhurnal Organicheskoi Khimii, 2023, Vol. 59, No. 5, pp. 640–647 https://doi.org/10.31857/S0514749223050117.

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Kayukov, Y.S., Grigor’ev, A.A., Karpov, S.V. et al. Heterocyclization of 2-Nitrobenzoyl-1,1,3,3-tetracyanopropenides under the Action of Hydrogen Chloride in Alcohol. Russ J Org Chem 59, 813–819 (2023). https://doi.org/10.1134/S1070428023050111

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