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Alkylation of 3-cyano-4-methoxymethyl-6-methyl-2(1h)-pyridone by active halomethylene compounds. The molecular structure of 3-amino-2-benzoyl-4-methoxymethyl-6-methylfuro[2,3-b]pyridine

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Abstract

The alkylation of 3-cyano-4-methoxymethyl-6-methyl-2(1H)-pyridone by active halomethylene compounds has been studied. It was shown that the reaction of the pyridone with methyl- and ethylchloroacetates and phenacyl and p-bromophenacyl bromides occurs to give N- and O-structural isomers. Only the N-derivatives are separated from the reaction mixture when the pyridone is alkylated with iodoacetamide. It was found that 2-aroylmethyl-3-cyano-4-methoxymethyl-6-methylpyridines cyclize in the presence of KOH to 3-amino-2-aroyl-4-methoxymethyl-6-methylfuro[2,3-b]pyridines. The molecular structure of 3-amino-2-benzoyl-4-methoxymethyl-6-methylfuro[2,3-b]pyridine has been studied using an X-ray analytical method.

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Authors and Affiliations

  1. Kuban State Technological University, 350072, Krasnodar, Russia

    E. A. Kaigorodova, V. K. Vasilin, E. A. Sidorova, V. E. Zavodnik & G. D. Krapivin

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  1. E. A. Kaigorodova
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  2. V. K. Vasilin
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  3. E. A. Sidorova
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  4. V. E. Zavodnik
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  5. G. D. Krapivin
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1670–1682, November, 2004.

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Kaigorodova, E.A., Vasilin, V.K., Sidorova, E.A. et al. Alkylation of 3-cyano-4-methoxymethyl-6-methyl-2(1h)-pyridone by active halomethylene compounds. The molecular structure of 3-amino-2-benzoyl-4-methoxymethyl-6-methylfuro[2,3-b]pyridine. Chem Heterocycl Compd 40, 1442–1453 (2004). https://doi.org/10.1007/s10593-005-0063-1

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  • DOI: https://doi.org/10.1007/s10593-005-0063-1

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