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Chemistry of Heterocyclic Compounds

, Volume 11, Issue 9, pp 1107–1112 | Cite as

Reactions of 6-methoxy-1,2,3,4-tetrahydro-β-carbolin-1-ones and their dichlorophosphoryl-substituted derivatives with acetic anhydride

Synthesis of 5-acetyl derivatives of the β-carboline series
  • L. N. Yakhontov
  • M. Ya. Uritskaya
  • O. S. Anisimova
  • T. Ya. Filipenko
  • K. F. Turchin
  • E. M. Peresleni
  • Yu. N. Sheinker
Article
  • 23 Downloads

Abstract

2-Benzyl-, 9-benzyl-, and 2,9-dibenzyl-6-methoxy-1,2,3,4-tetrahydro-β-carbolin-1-ones were synthesized. It is shown that 6-methoxy-1,2,3,4-tetrahydro-β-carbolin-1-one and its 2- and 9-monobenzyl-substituted derivatives react with phosphorus oxychloride to give dichlorophosphoryl derivatives in which the dichlorophosphoryl residue enters into the composition of the cation and is bonded to the oxygen in the 1 position or (in the case of the pyrrole-nitrogen-unsubstituted compounds) the nitrogen atom in the 9 position. The possibility of acetylation of the dichlorophosphoryl compounds in the 5 position with acetic anhydride under mild conditions to give high yields of products was observed. The regularities in the mass spectra and PMR spectra of the β-carbolinone derivatives were exposed.

Keywords

Oxygen Nitrogen Acetic Phosphorus Mass Spectrum 
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.

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Copyright information

© Plenum Publishing Corporation 1976

Authors and Affiliations

  • L. N. Yakhontov
    • 1
  • M. Ya. Uritskaya
    • 1
  • O. S. Anisimova
    • 1
  • T. Ya. Filipenko
    • 1
  • K. F. Turchin
    • 1
  • E. M. Peresleni
    • 1
  • Yu. N. Sheinker
    • 1
  1. 1.S. Ordzhonikidze All-Union Scientific-Research Pharmaceutical-Chemistry InstituteMoscow

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