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Methyl nitroacetate and 3-nitropropionate in the synthesis of hexahydropyrimidines and piperidines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Treatment of methyl nitroacetate and 3-nitropropionate with formaldehyde and primary amines under Mannich reaction conditions gives 5-nitrohexahydropyrimidines. In the case of methyl nitroacetate both the 5-nitrohexahydropyrimidine and isomeric 3,5-di(methoxycarbonyl)-1-methyl-3,5-dinitropiperidines are formed.

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Authors and Affiliations

  1. Institute of Organic Chemistry, Ufa Science Center of the Russian Academy of Sciences, Ufa, 450054, Russia

    R. R. Shakirov, N. M. Vlasova & N. Z. Baibulatova

  2. Bashkir State University, Ufa, 450074, Russia

    T. V. Dokichev, R. Z. Biglova & R. F. Talipov

Authors
  1. R. R. Shakirov
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  2. T. V. Dokichev
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  3. R. Z. Biglova
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  4. N. M. Vlasova
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  5. N. Z. Baibulatova
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  6. R. F. Talipov
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Corresponding author

Correspondence to T. V. Dokichev.

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__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 53–60, January, 2008.

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Shakirov, R.R., Dokichev, T.V., Biglova, R.Z. et al. Methyl nitroacetate and 3-nitropropionate in the synthesis of hexahydropyrimidines and piperidines. Chem Heterocycl Comp 44, 43–49 (2008). https://doi.org/10.1007/s10593-008-0011-y

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  • DOI: https://doi.org/10.1007/s10593-008-0011-y

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