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Lactam acetals

XI. Reactions of N-methyl-2-pyrrolidone diethylacetal with some nucleophilic and electrophilic reagents

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It is shown in the case of the reaction of N-methylbutyro-, N-methylvalero-, and N-methylcaprolactam diethylacetals with benzyl cyanide that the five-membered acetal is the most reactive in the reaction with compounds having an active methylene link. 1-Methyl-3-(Ωphenyl-Ω-benzoxymethylene)-2-pyrrolidone is primarily formed in the reaction of N-methyl-2-pyrrolidone diethylacetal with C6H5COCl. The reaction of N-methylcaprolactam diethylacetal with acrylonitrile gives a mixture of N-methylcaprolactam, 1-methyl-2-ethoxy-3-(Β-cyanoethyl)-4, 5,6,7-tetrahydroazepine, and 2-methyl-1,9-dehydro-9-cyano-2-azabicyclo-[5.2.0] nonane.

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Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical-Chemistry Institute, Moscow

    A. M. Zhidkova, V. G. Granik, N. S. Kuryatov, V. P. Pakhomov, O. S. Anisimova & R. G. Glushkov

Authors
  1. A. M. Zhidkova
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  2. V. G. Granik
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  3. N. S. Kuryatov
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  4. V. P. Pakhomov
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  5. O. S. Anisimova
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  6. R. G. Glushkov
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Additional information

For Communication X see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1089–1093, August, 1974.

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Zhidkova, A.M., Granik, V.G., Kuryatov, N.S. et al. Lactam acetals. Chem Heterocycl Compd 10, 947–950 (1974). https://doi.org/10.1007/BF00487117

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  • DOI: https://doi.org/10.1007/BF00487117

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