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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
Article

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.

Keywords

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

References

  1. 1.
    V. K. Srivastava, A. Joharapurkar, S. Raval, J. Z. Patel, R. Soni, P. Raval, A. Gite, A. Goswami, N. Sadhwani, N. Gandhi, H. Patel, B. Mishra, M. Solanki, B. Pandey, M. R. Jain, and P. R. Patel, J. Med. Chem., 50, 5951 (2007).CrossRefGoogle Scholar
  2. 2.
    Y. L. Bennani, M. G. Campbell, D. Dastrup, and E. P. Huck, US Pat. Appl. 20070197526.Google Scholar
  3. 3.
    A. V. Kurkin, A. A. Utkina, and M. A. Yurovskaya, Khim. Geterotsikl. Soed., 127 (2008). [Chem. Heterocycl. Compd., 44, 106 (2008)].Google Scholar
  4. 4.
    B. List, J. Am. Chem. Soc., 124, 5656 (2002).CrossRefGoogle Scholar
  5. 5.
    N. Kumaragurubaran, K. Juhl, W. Zhaung, A. Bogevig, and K. A. Jorgensen, J. Am. Chem.. Soc., 124, 6254 (2002).CrossRefGoogle Scholar
  6. 6.
    Y. Hayashi, S. Aratake, Y. Imai, K. Hibino, Q.-Y. Chen, J. Yamaguchi, and T. Uchimaru, Chem. Asian J., 3, 225 (2008).CrossRefGoogle Scholar
  7. 7.
    R. S. Alekseev, A. V. Kurkin, and M. A. Yurovskaya, Khim. Heterotsikl. Soed., 706 (2011).[Chem. Heterocycl. Compd., 47, 584 (2011)].Google Scholar

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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