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


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.


Ethyl Pyrolysis Ketone Palladium Indole 
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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

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