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Reactions of Ethyl 2-Amino-5-(2-aryl-2-oxoethylidene)- 4-oxo-4,5-dihydrofuran-3-carboxylates and 2-Amino-5-(2-aryl- 2-oxoethylidene)-4-oxo-4,5-dihydrofuran-3-carbonitriles with Alcohols

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Abstract

Ethyl 2-amino-5-(2-aryl-2-oxoethylidene)-4-oxo-1H-4,5-dihydrofuran-3-carboxylates and 2-amino- 5-(2-aryl-2-oxoethylidene)-4-oxo-1H-4,5-dihydrofuran-3-carbonitriles reacted with alcohols in the presence of a catalytic amount of concentrated aqueous HCl to give the corresponding 5-alkoxy-2-amino-5-(2-aryl-2- oxoethyl)-4-oxo-1H-4,5-dihydrofuran-3-carboxylic acid derivatives. A probable reaction mechanism was proposed on the basis B3LYP/6-311G(d) quantum chemical calculations.

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Authors and Affiliations

  1. Perm National State Research University, ul. Bukireva 15, Perm, 614990, Russia

    D. V. Ivanov, S. N. Shurov & M. V. Dmitriev

  2. Perm State Pharmaceutical Academy, Ministry of Health of the Russian Federation, ul. Polevaya 2, Perm, 614990, Russia

    D. V. Ivanov & N. M. Igidov

  3. Research Institute of Chemistry, Lobachevskii Nizhny Novgorod State University, pr. Gagarina 23, Nizhny Novgorod, 603950, Russia

    I. N. Chernov

Authors
  1. D. V. Ivanov
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  2. N. M. Igidov
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  3. S. N. Shurov
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  4. M. V. Dmitriev
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  5. I. N. Chernov
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Correspondence to D. V. Ivanov.

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Original Russian Text © D.V. Ivanov, N.M. Igidov, S.N. Shurov, M.V. Dmitriev, I.N. Chernov, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 4, pp. 572–576.

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Ivanov, D.V., Igidov, N.M., Shurov, S.N. et al. Reactions of Ethyl 2-Amino-5-(2-aryl-2-oxoethylidene)- 4-oxo-4,5-dihydrofuran-3-carboxylates and 2-Amino-5-(2-aryl- 2-oxoethylidene)-4-oxo-4,5-dihydrofuran-3-carbonitriles with Alcohols. Russ J Org Chem 54, 573–577 (2018). https://doi.org/10.1134/S1070428018040097

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  • DOI: https://doi.org/10.1134/S1070428018040097

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