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Chemical transformations of 3-aminopyrrolidin-2-ones of the norbornane and cyclopropane series

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3-Aminopyrrolidin-2-ones containing a fused norbornane or spirocyclopropane fragment react with benzaldehyde to give azomethines, which can be transformed into N-substituted 3-aminopyrrolidin-2-ones by reduction with sodium borohydride. Diazotization of amino-pyrrolidinones with NaNO2 in acetic acid results in the elimination of molecular nitrogen and in the formation of acetoxy or unsaturated derivatives (through stabilization of intermediate carbocations). 6-Methylidene4-azaspiro[2.4]heptan-5-one obtained by diazotization of 6-amino-6-methyl-4-azaspiro[2.4]heptan-5-one easily reacts with diazomethane, diazocyclo-propane, and benzonitrile oxide to yield heterocyclic spiranes by means of 1,3-dipolar cycloaddition.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    I. V. Kostyuchenko, E. V. Shulishov, R. R. Rafikov, A. I. Novichkov & Yu. V. Tomilov

  2. Institute of Organic Chemistry, Ufa Research Center of the Russian Academy of Sciences, 71 prosp. Oktyabrya, 450054, Ufa, Russian Federation

    V. A. Dokichev

Authors
  1. I. V. Kostyuchenko
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  2. E. V. Shulishov
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  3. R. R. Rafikov
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  4. A. I. Novichkov
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  5. V. A. Dokichev
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  6. Yu. V. Tomilov
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Corresponding authors

Correspondence to V. A. Dokichev or Yu. V. Tomilov.

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On the occasion of the 75th anniversary of the foundation of the N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 337–343, February, 2009.

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Kostyuchenko, I.V., Shulishov, E.V., Rafikov, R.R. et al. Chemical transformations of 3-aminopyrrolidin-2-ones of the norbornane and cyclopropane series. Russ Chem Bull 58, 339–346 (2009). https://doi.org/10.1007/s11172-010-0013-7

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  • DOI: https://doi.org/10.1007/s11172-010-0013-7

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