Chemistry of Heterocyclic Compounds

, Volume 20, Issue 7, pp 713–716 | Cite as

Synthesis and some electrophilic substitution reactions of 2-phenyloxazole

  • L. I. Belen'kii
  • M. A. Cheskis


A new synthesis of 2-phenyloxazole that includes the preparation of 2-phenyloxazoline and aromatization of the latter by the action of nickel peroxide was developed. It was established that under conditions that exclude protonation electrophilic substitution reactions are directed to the oxazole ring of 2-phenyloxazole; the 5 position is considerably more active than the 4 position.


Nickel Peroxide Organic Chemistry Substitution Reaction Aromatization 
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.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    R. Lakhan and B. Ternai, Adv. Heterocycl. Chem., 17, 99 (1974).Google Scholar
  2. 2.
    I. Turchi and M. I. S. Dewar, Chem. Rev., 75, 389 (1975).Google Scholar
  3. 3.
    P. B. Terent'ev and N. P. Lomakina, Khim. Geterotsikl. Soedin., No. 5, 579 (1976).Google Scholar
  4. 4.
    I. Turchi, Ind. Eng. Chem. Prod. Res. Dev., 20, 32. (1981).Google Scholar
  5. 5.
    J. J. Rosenbaum and W. E. Cass, J. Am. Chem. Soc., 64, 2444 (1942).Google Scholar
  6. 6.
    R. Gompper and O. Christmann, Chem. Ber., 92, 1944 (1959).Google Scholar
  7. 7.
    R. Gompper and H. Rühle, Ann. Chem., 626, 83 (1959).Google Scholar
  8. 8.
    N. Saito, T. Kirihara, K. Yamanaka, S. Tsuruta, and S. Tasuda, J. Pharm. Soc., Jpn., 88, 1289 (1968); Ref. Zh. Khim., 12Zh428 (1969).Google Scholar
  9. 9.
    I. Simiti and E. Chindris, Arch. Pharm., 305, 509 (1972).Google Scholar
  10. 10.
    O. P. Shvaika and G. P. Klimisha, Khim. Geterotsikl. Soedin., No. 1, 19 (1966).Google Scholar
  11. 11.
    C. Makkay and J. Literati-Kiraly, Stud. Univ. Babes-Bolyai, Chem., 23, No. 2, 52 (1978); Ref. Zh. Khim. 22Zh302 (1979).Google Scholar
  12. 12.
    D. L. Evans, D. K. Minster, U. Jordis, S. M. Hecht, A. L. Mazzu, and A. L. Meyers, J. Org. Chem., 44, 497 (1979).Google Scholar
  13. 13.
    US Patent No. 3402178; Chem. Abstr., 69, 96750 (1968).Google Scholar
  14. 14.
    K. Nakagawa, K. Konaka, and T. Nakata, J. Org. Chem., 27, 1597 (1962).Google Scholar
  15. 15.
    P. G. Ferrini and A. Marker, Angew. Chem., 75, 165 (1963).Google Scholar
  16. 16.
    M. T. Leffler and R. Adams, J. Am. Chem. Soc., 59, 2252 (1977).Google Scholar
  17. 17.
    E. V. Brown, J. Org. Chem., 42, 3208 (1977).Google Scholar

Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • L. I. Belen'kii
    • 1
  • M. A. Cheskis
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

Personalised recommendations