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Russian Chemical Bulletin

, Volume 64, Issue 1, pp 142–145 | Cite as

Synthesis of benzoic acids containing a 1,2,4-oxadiazole ring

  • G. G. Krasouskaya
  • A. S. Danilova
  • S. V. Baikov
  • A. V. Kolobov
  • E. R. KofanovEmail author
Full Articles

Abstract

A new approach to the synthesis of 4and 3-(5-R-1,2,4-oxadiazol-3-yl)benzoic acids via a selective oxidation of 5-R-3-tolyl-1,2,4-oxadiazoles with air oxygen in the presence of a catalytic system based on cobalt acetate was suggested. This synthesis allowed us to obtain the products in higher yields and with shorter sequence of steps as compared to the known procedures.

Keywords

1,2,4-oxadiazole catalytic oxidation methylarenes benzoic acids 

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References

  1. 1.
    Sh. Kitamura, H. Fukushi, T. Miyawaki, M. K. Awamura, Z. T. Erashita, T. N. Aka, Chem. Pharm. Bull., 2001, 49, 268.CrossRefGoogle Scholar
  2. 2.
    M. Frizler, F. Lohr, N. Furtmann, J. Kläs, M. Gütschow, J. Med. Chem., 2011, 54, 396.CrossRefGoogle Scholar
  3. 3.
    J. Chen, B. Levant, Sh. Wang, Bioorg. Med. Chem. Lett., 2012, 22, 5612.CrossRefGoogle Scholar
  4. 4.
    R. H. Tale, A. H. Rodge, A. P. Keche, G. D. Hatnapure, P. R. Padole, G. S. Gaikwad, S. S. Turkar, J. Chem. Pharm. Res., 2011, 3, 496.Google Scholar
  5. 5.
    E. M. Welch, E. R. Barton, J. Zhuo, P. Trifillis, S. Paushkin, M. Patel, C. R. Trotta, S. Hwang, R. G. Wilde, G. Karp, J. Takasugi, G. Chen, S. Jones, H. Ren, Y. C. Moon, D. Corson, A. A. Turpoff, J. A. Campbell, M. M. Conn, A. Khan, N. G. Almstead, J. Hedrick, A. Mollin, N. Risher, M. Weetall, S. Yeh, A. A. Branstrom, J. M. Colacino, J. Babiak, W. D. Ju, S. Hirawat, V. J. Northcutt, L. L. Miller, P. Spatrick, F. He, M. Kawana, H. Feng, A. Jacobson, S. W. Peltz, H. L. Sweeney, Nature, 2007, 447, 87.CrossRefGoogle Scholar
  6. 6.
    D. R. dos Santos, A. G. de Oliveira, R. L. Coelho, I. M. Begnini, R. F. Magnago, L. da Silvaet, ARKIVOC, 2008, 17, 157.Google Scholar
  7. 7.
    Ivan H. R. Tomi, J. Saudi Chem. Soc., 2012, 16, 153.CrossRefGoogle Scholar
  8. 8.
    S. V. Baikov, M. V. Karunnaya, V. V. Sosnina, G. G. Krasouskaya, A. S. Danilova, E. R. Kofanov, Izv. Vuzov. Khim. i Khim. Tekhnol. [Bull. Higher Ed. Inst. Chem and Chem. Technol., 2012, 55, 80 (in Russian).Google Scholar
  9. 9.
    S. V. Baikov, A. A. Bakanova, G. G. Krasouskaya, E. R. Kofanov, Izv. Vuzov. Khim. i Khim. Tekhnol. [Bull. Higher Ed. Inst. Chem. and Chem. Technol.], 2013, 56, 13 (in Russian).Google Scholar
  10. 10.
    Ya. Yoshino, Yo. Hayashi, T. Iwahama, S. Sakaguchi, Y. Ishii, J. Org. Chem., 1997, 62, 6810.CrossRefGoogle Scholar
  11. 11.
    R. A. F. Tomas, J. C. M. Bordado, J. F. P. Gomes, Chem. Rev., 2013, 113, 7421.CrossRefGoogle Scholar
  12. 12.
    WO Pat. 2007123936; http://ep.espacenet.com.Google Scholar
  13. 13.
    J. C. Jochims, in Comprehensive Heterocyclic Chemistry. Vol. Five-Membered Rings with More Than Two Heteroatoms and Fused Carbocyclic Derivatives, Ed. A. R. Katritzky, Pergamon, Oxford, 1996, p. 185.Google Scholar
  14. 14.
    H. Gallardo, I. M. Begnini, Mol. Cryst. Liq. Cryst., 1995, 258, 85.CrossRefGoogle Scholar
  15. 15.
    O. B. Laskina, S. F. Mel’nikova, I. V. Tselinkii, Russ. J. Org. Chem., 2012, 48, 278 [Zh. Org. Khim., 2012, 48, 286–291].CrossRefGoogle Scholar
  16. 16.
    Q. Zeng, J. G. Allen, M. P. Bourbeau, X. Wanga, G. Yaoa, S. Tadessea, J. T. Ridera, C. C. Yuana, F.-T. Honga, M. R. Leea, S. Zhangb, J. A. Lofgrenb, D. J. Freemanb, S. Yangb, C. Lic, E. Tomineyc, X. Huangd, D. Hoffmane, H. K. Yamanef, C. Fotscha, C. Domingueza, R. Hungatea, X. Zhangb, Bioorg. Med. Chem. Lett., 2010, 20, 1559.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • G. G. Krasouskaya
    • 1
  • A. S. Danilova
    • 1
  • S. V. Baikov
    • 2
  • A. V. Kolobov
    • 1
  • E. R. Kofanov
    • 1
    Email author
  1. 1.Yaroslavl State Technical UniversityYaroslavlRussian Federation
  2. 2.K. D. Ushinsky Yaroslavl State Pedagogical UniversityYaroslavlRussian Federation

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