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Chemistry of Heterocyclic Compounds

, Volume 8, Issue 4, pp 463–467 | Cite as

Effect of catalysts on the Fischer cyclization of cyclohexanone 4-pyridylhydrazone

  • L. N. Yakhontov
  • M. F. Marshalkin
  • O. S. Anisimova
Article
  • 40 Downloads

Abstract

The peculiarities of the Fischer cyclization of cyclohexanone 4-pyridylhydrazone and the formation of 5,6,7,8-tetrahydro-γ-carboline, 4-aminopyridine, 4-ethylaminopyridine, 4-pyridone, and 2-(4-pyridyl)-3,3a,4,5,6,7-hexahydroindazole-3-spirocyclohexane under the conditions of this reaction are examined. In the case of I, as also for the isomeric 2-pyridylhydrazones, catalysts can be arranged in the following order with respect to their ability to increase the yield of the normal indolyzation product: cuprous chloride ≈ sulfosalicyclic acid < polyphosphoric acid < p-toluenesulfonic acid < zinc chloride. It was established that the indolyzation of I proceeds also without acid catalysts under the influence of sodium ethoxide.

Keywords

Sodium Chloride Zinc Organic Chemistry Acid Catalyst 
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

© Consultants Bureau 1974

Authors and Affiliations

  • L. N. Yakhontov
    • 1
  • M. F. Marshalkin
    • 1
  • O. S. Anisimova
    • 1
  1. 1.S. Ordzhonikidze All-Union Scientific-Research Institute of Pharmaceutical ChemistryMoscow

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