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Acetals of lactams and acid amides. 48. Reaction of enamino diketones with amide crystals. Synthesis of derivatives of coumarin and carbostyril

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

It was established that the reaction of derivatives of 2-aminomethylenecyclohexane-1,3-dione with N,N-dimethyl-diethylacetal gives dienediamines, heating of which in aqueous hydrochloric acid leads, depending on the structure, to derivatives of carbostyril and/or coumarin. This unusual reaction is based on initial attack at the α position of the enamino diketone by the ketone acetal, which exists in equilibrium with the starting amide acetal.

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Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical-Chemistry Institute, 119815, Moscow

    V. G. Grannik, A. K. Shanazarov, N. P. Solov'eva, V. V. Chistyakov, I. V. Persianova & Yu. N. Sheinker

Authors
  1. V. G. Grannik
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  2. A. K. Shanazarov
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  3. N. P. Solov'eva
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  4. V. V. Chistyakov
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  5. I. V. Persianova
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  6. Yu. N. Sheinker
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Additional information

See [1] for Communication 47.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1470–1476, November, 1987.

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Grannik, V.G., Shanazarov, A.K., Solov'eva, N.P. et al. Acetals of lactams and acid amides. 48. Reaction of enamino diketones with amide crystals. Synthesis of derivatives of coumarin and carbostyril. Chem Heterocycl Compd 23, 1171–1177 (1987). https://doi.org/10.1007/BF00479362

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  • DOI: https://doi.org/10.1007/BF00479362

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