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Acetals of lactams and acid amides. 47. Investigation of the behavior of substituted 6-(Β-dimethylamino) vinyl-4-pyrimidinones in acidic media. Synthesis of 3-cyano-4-anilino-5-formyl-2-pyridone and 3-chloro-4-cyanobenzo[b] [1,6]-naphthyridine

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Abstract

The hydrolysis of 1-substituted 5-cyano-6-(Β-dimethylamino)vinyl-4-pyrimidinones in acidic media was studied. It was shown that the 1-benzyl derivative is converted to a mixture of α-cyano-Β-benzylamino-crotonamide and 3-cyano- and 3-carbamido-4-benzyl-amino-2-pyridones. The principal product in the hydrolysis of the 1-phenyl derivative is 3-cyano-4-anilino-5-formyl-2-pyridone. Cyclization of the latter by heating in phosphorus oxychloride leads to 3-chloro-4-cyanobenzo[b] [1, 6]naphthyr idine.

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Authors and Affiliations

  1. S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical Chemistry, 119021, Moscow

    N. Z. Yalysheva, N. P. Solov'eva, V. V. Chistyakov, Yu. N. Sheinker & V. G. Granik

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  1. N. Z. Yalysheva
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  2. N. P. Solov'eva
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  3. V. V. Chistyakov
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  4. Yu. N. Sheinker
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  5. V. G. Granik
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Additional information

See [1] for Communication 46.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1118–1123, August, 1986.

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Yalysheva, N.Z., Solov'eva, N.P., Chistyakov, V.V. et al. Acetals of lactams and acid amides. 47. Investigation of the behavior of substituted 6-(Β-dimethylamino) vinyl-4-pyrimidinones in acidic media. Synthesis of 3-cyano-4-anilino-5-formyl-2-pyridone and 3-chloro-4-cyanobenzo[b] [1,6]-naphthyridine. Chem Heterocycl Compd 22, 909–914 (1986). https://doi.org/10.1007/BF01175070

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  • DOI: https://doi.org/10.1007/BF01175070

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