Advertisement

Chemistry of Heterocyclic Compounds

, Volume 1, Issue 2, pp 153–156 | Cite as

Indole derivatives. I.β-(3-indolyl) ketones

  • A. A. Semeno
  • I. V. Terent'eva
Article
  • 48 Downloads

Abstract

A number of α-skatyl-α-substituted acetoacetic esters (ethyl, tert. -butyl, and benzyl) are prepared by treating gramine with sodium derivatives of α-substituted acetoacetic esters. When ethyl α-alkyl-α-skatylacetoacetates are heated with dilute alkali, they are split into indole and a substituted acetoacetic ester, while saponification with concentrated alcoholic alkali gives α-substitutedβ-(3-indolyl)propionic acids. 3-Skatyl-heptan-2-one can be obtained by pyrolysis of 3-skatyl-3-carbo-tert. -butoxyheptan-2-one, or by hydrogenolysis of 3-skatyl-3-carbobenzoxyheptan-2-one over a palladium catalyst. Alkylation of cycloheptanone and cyclohexanone enamines by gramine gives cyclicβ-(3-indolyl)ketones, viz., 2-skatylcyclopentanone and 2-skatylcyclohexanone.

Keywords

Ethyl Pyrolysis Ketone Palladium Indole 
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.

References

  1. 1.
    J. Sczmuszkovitcz, J. Am. Chem. Soc., 79, 2819, 1957. J. R. Merchant and S. S. Salgar, J. Indian Chem. Soc., 40, 83, 1963.Google Scholar
  2. 2.
    D. O. Holland and J. H. R. Nayler, J. Chem. Soc., 280, 1953. E. Hardegger and H. Corrodi, Helv. Chim. Acta, 39, 514, 1956. R. Lukeš and K. Blaha, Chem. Listy, 50, 2036, 1956.Google Scholar
  3. 3.
    H. Plieninger and S. Tadashi, Ber., 88, 55, 1955.Google Scholar
  4. 4.
    G. Näslund and S-O. Lavesson, Acta Chem. Scand., 16, 1191, 1324, 1962.Google Scholar
  5. 5.
    V. I. Gunar, Izv. AN SSSR, OKhN, 1110, 1963.Google Scholar
  6. 6.
    Z. Procházka, Chem. Listy, 53, 922, 1959.Google Scholar

Copyright information

© The Faraday Press, Inc. 1966

Authors and Affiliations

  • A. A. Semeno
    • 1
  • I. V. Terent'eva
    • 1
  1. 1.Institute of Chemistry AS Moldavian SSRKishinev

Personalised recommendations