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C-acylation of heterocyclic keto-enols Communication 8. 3-acyl-4-hydroxy-6-methyl-2(lH)-pyridones and their 1-methyl derivatives

  • Organic and Biological Chemistry
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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The acetylation of 4-hydroxy-6-methyl-2(1H)-pyridone and its 1-methyl derivative was studied. By the action of acetic acid in presence of phosphoryl chloride, from the first substance the C-acetylation product -3-acetyl-4-hydroxy-6-methyl-2(1H)-pyridone- was obtained, and from the second substance the O-acetylation product -4-acetoxy-l,6-dimethyl-2(1H)-pyridone- was obtained. In presence of polyphosphoric acid the C-acylation product was obtained in both cases.

  2. 2.

    The structure of the C-acetylation products was proved by independent syntheses and a comparison of the IR spectra.

  3. 3.

    The general character of the C-acylation reaction of 4-hydroxy-6-methyl-2(lH)-pyridone with aliphatic acids in presence of polyphosphoric acid was confirmed by the preparation of a number of its 3-acyl derivatives, the structure of which was proved on the basis of the UV and IR spectra.

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Authors and Affiliations

  1. Institute of Chemistry of Natural Products, Academy of Sciences of the USSR, USSR

    N. S. Vul'fson, G. M. Sukhotina & V. N. Zheltova

  2. Institute of Organic Intermediate Products and Dyes, USSR

    N. S. Vul'fson, G. M. Sukhotina & V. N. Zheltova

Authors
  1. N. S. Vul'fson
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  2. G. M. Sukhotina
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  3. V. N. Zheltova
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 887–891, May, 1966.

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Vul'fson, N.S., Sukhotina, G.M. & Zheltova, V.N. C-acylation of heterocyclic keto-enols Communication 8. 3-acyl-4-hydroxy-6-methyl-2(lH)-pyridones and their 1-methyl derivatives. Russ Chem Bull 15, 848–851 (1966). https://doi.org/10.1007/BF00849385

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  • DOI: https://doi.org/10.1007/BF00849385

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