Chemistry of Heterocyclic Compounds

, Volume 48, Issue 2, pp 327–333 | Cite as

Use of the α-amination reaction for the synthesis of pyrazole derivatives containing carbo- and heterocyclic substituents on the nitrogen atom

  • A. A. UtkinaEmail author
  • A. V. Kurkin
  • M. A. Yurovskaya

A method has been developed for the synthesis of pyrazoles with carbo- and heterocyclic substituents on the nitrogen atom based on the α-amination reaction of carbo- and heterocyclic ketones, using azodicarboxylate–L-proline system with subsequent interaction with malonodialdehyde tetramethyl-acetal. In the case of carbocyclic ketones and tetrahydro-γ-pyranone, the reaction occurs stereo-selectively to give chiral hydrazines and pyrazoles. With derivatives of piperidin-4-one, α-amination is accompanied by racemization.


azodicarboxylate cyclohexanone cyclopentanone N-substituted piperidones pyrazoles L-proline tetrahydro-γ-pyranone stereoselective α-amination 


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Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • A. A. Utkina
    • 1
    Email author
  • A. V. Kurkin
    • 1
  • M. A. Yurovskaya
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityMoscowRussia

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