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β-Dicarbonyl compounds

Communication 26. Chemical properties and biological activity of enamines derived from β-dicarbonyl compounds

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

Conclusions

  1. 1.

    When treated with methyl iodide in tetrahydrofuran, the sodium derivative of 3-(cyclohexylamino)-2-cyclohexen-1-one undergoes C- and N-methylation.

  2. 2.

    When heated with acetic anhydride, 3-(cyclohexylamino)-2-cyclohexen-1-one and 2-[(cyclohexylamino)methylene]cyclohexanone form C-and N-acetyl derivatives respectively.

  3. 3.

    1,3-Cyclohexanedione and its 5,5-dimethyl derivative react with acetoacetamides with formation of 7,8-dihydro-4-methyl-and 7,8-dihydro-4,7,7-trimethy1-2H-1-benzopyran-2,5(6H)-diones respectively.

  4. 4.

    Enamines derived fromβ-diketones have a weak toxic action in vitro toward some species of infusorians, mollusks, fish, and ascarids.

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Literature cited

  1. L. P. Vinogradova and S. I. Zav'yalov, Izv. SN SSSR, Ser. khim.,1966, 1795.

  2. K. Hamamoto, T. Isojima, and M. Yoshioka, Japanese Patent 6,175 (61), 1957; Chem. Abstrs.,58, 110177 (1963).

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  3. L. P. Vinogradova, G. A. Kogan, and S. I. Zav'yalov, Izv. AN SSSR, Ser. khim.,1964, 1054.

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Authors and Affiliations

  1. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR, USSR

    G. V. Kondrat'eva, V. I. Gunar, L. F. Ovechkina, S. I. Zav'yalov & A. I. Krotov

  2. Institute of Malaria, Medical Parasitology, and Helminthology, Ministry of Health, USSR

    G. V. Kondrat'eva, V. I. Gunar, L. F. Ovechkina, S. I. Zav'yalov & A. I. Krotov

Authors
  1. G. V. Kondrat'eva
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  2. V. I. Gunar
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  3. L. F. Ovechkina
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  4. S. I. Zav'yalov
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  5. A. I. Krotov
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 3, pp. 633–639, March, 1967.

We are deeply indebted to G. A. Kogan for carrying out the spectral investigations.

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Kondrat'eva, G.V., Gunar, V.I., Ovechkina, L.F. et al. β-Dicarbonyl compounds. Russ Chem Bull 16, 609–614 (1967). https://doi.org/10.1007/BF00906003

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  • DOI: https://doi.org/10.1007/BF00906003

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