Advertisement

Chemistry of Heterocyclic Compounds

, Volume 18, Issue 10, pp 1008–1011 | Cite as

Chemistry of oxalyl derivatives of methyl ketones. 28. Reaction of carbonyl compounds of adamantane with 5-phenyl-2,3--dihydrofuran-2,3-dione

  • Yu. S. Andreichikov
  • M. P. Sivkova
  • N. N. Shapet'ko
Article
  • 27 Downloads

Abstract

The reaction of substituted methyl 1-adamantyl ketones with an equimolar amount of 5-phenyl-2,3-dihydrofuran-2,3-dione under the conditions of the thermal decarbonylation of the latter leads to the corresponding 2-methyl-2-adamantyl-6-pheny1-1,3-dioxen-4-ones, 6-phenyl-3-benzoyl-2,4-dione, and the starting ketones. The steric and electronic factors that affect the yields of the dioxen-4-ones were examined. α-Hydroxymethyl 1-adamantyl ketones open up the furan ring to give 1-adamantoylmethyl benzoylpyruvate. Data from the IR, PMR, and UV spectra are presented.

Keywords

Carbonyl Ketone Dione Furan Carbonyl Compound 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    Yu. S. Andreichikov, L. F. Gein, and G. D. Plakhina, Zh. Org. Khim., 16, 2336 (1980).Google Scholar
  2. 2.
    Yu. S. Andreichikov, Yu. A. Nalimova, A. P. Kozlov, and I. A. Rusakov, Zh. Org, Khim., 14, 2436 (1978).Google Scholar
  3. 3.
    Yu. S. Andreichikov, S. P. Tendryakova, Yu. A. Nalimova, and G. D. Plakhina, Khim. Geterotsikl. Soedin., No. 8, 1030 (1977).Google Scholar
  4. 4.
    Yu. S. Andreichikov, S. G. Pitirimova, R. F. Saraeva, V. L. Gein, G. D. Plakhina, and L. A. Voronova, Khim. Geterotsikl. Soedin., No. 3, 407 (1978).Google Scholar
  5. 5.
    L. N. Kurovskaya, N. N. Shapte'ko, Yu. S. Andreichikov, and R. F. Saraeva, Zh. Strukt. Khim., 13, 1026 (1972).Google Scholar
  6. 6.
    A. L. Fridman, V. S. Zalesov, L. O. Kon'shina, N. A. Kolobov, K. V. Dolbilkin, I. K. Moiseev, T. A. Mratkhuzina, and P. G. Belyaev, Khim.-farm. Zh., No. 4, 35 (1976).Google Scholar
  7. 7.
    A. L. Fridman, M. P. Sivkova, V. S. Zalesov, K. V., Dolbilkin, I. K. Moiseev, R. I. Doroshenko, and É. V. Manzhlevskaya, Khim.-farm. Zh., No. 12, 24 (1979).Google Scholar
  8. 8.
    A. L. Fridman, N. A. Kolobov, G. S. Ismagilova, and V. S. Zalesov, Trudy Permsk. Farm. Inst., No. 8, 18 (1974).Google Scholar
  9. 9.
    Yu. S. Andreichikov, Yu. A. Nalimova, G. D. Plakhina, R. F. Saraeva, and S. P. Tendrykova, Khim. Geterotsikl. Soedin., No. 11, 1468 (1975).Google Scholar

Copyright information

© Plenum Publishing Corporation 1983

Authors and Affiliations

  • Yu. S. Andreichikov
    • 1
  • M. P. Sivkova
    • 1
  • N. N. Shapet'ko
    • 1
  1. 1.Perm State Pharmaceutical InstitutePerm

Personalised recommendations