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Synthesis of pyrrolidine and tetrahydroazonine derivatives from N-[bis(ethoxycarbonyl)methyl]tetrahydropyridinium bromide and methyl acetylenedicarboxylate

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Abstract

The reaction of N-methyl-N-(diethoxycarbonyl)methyltetrahydropyridinium bromide with dimethyl acetylenedicarboxylate in the presence of triethylamine at room temperature afforded 1,2-dimethyl 1-ethyl 2-[(3-vinyl-1-methyl-3-phenyl-2-ethoxycarbonyl)pyrrolidin-2-yl]-ethene-1,1,2-tricarboxylate in 25% yield. Its structure was proved by XRD analysis. At cooling to −20°C the pyrrolidine yield signifi cantly decreased and 3,4-dimethyl 2,2-diethyl 1-methyl-7-phenyl-1,5,8,9-tetrahydro-2H-azonine-2,2,3,4-tetratcarboxylate was obtained in 31% yield.

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Authors and Affiliations

  1. Russian University of Peoples Friendship, Moscow, 117198, Russia

    A. T. Soldatenkov, S. A. Soldatova, R. R. Suleimanov, K. B. Polyanskii & V. E. Kotsyuba

  2. Nesmeyanov Institute of Organoelemental Compounds, Russian Academy of Sciences, Moscow, Russia

    A. F. Smol’yakov, V. N. Khrustalev & M. Yu. Antipin

Authors
  1. A. T. Soldatenkov
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  2. S. A. Soldatova
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  3. R. R. Suleimanov
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  4. K. B. Polyanskii
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  5. V. E. Kotsyuba
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  6. A. F. Smol’yakov
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  7. V. N. Khrustalev
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  8. M. Yu. Antipin
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Corresponding author

Correspondence to A. T. Soldatenkov.

Additional information

Original Russian Text © A.T. Soldatenkov, S.A. Soldatova, R.R Suleimanov, K. B. Polyanskii, V.E. Kotsyuba, A.F. Smol’yakov, V.N. Khrustalev, M.Yu. Antipin, 2011, published in Zhurnal Organicheskoi Khimii, 2011, Vol. 47, No. 11, pp. 1700–1703.

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Soldatenkov, A.T., Soldatova, S.A., Suleimanov, R.R. et al. Synthesis of pyrrolidine and tetrahydroazonine derivatives from N-[bis(ethoxycarbonyl)methyl]tetrahydropyridinium bromide and methyl acetylenedicarboxylate. Russ J Org Chem 47, 1738–1741 (2011). https://doi.org/10.1134/S1070428011110157

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  • DOI: https://doi.org/10.1134/S1070428011110157

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