Skip to main content
SpringerLink
Log in

Synthesis and conversions of 2-acetyl-5-methyl-4-nitrofuran. Isomerization and beckman rearrangement of the oxime

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2-Acetyl-5-methyl-4-nitrofuran and 3,5-dinitro-α-methylfuran were obtained by the reaction of 70% nitric acid with 2-acetyl-5-methylfuran, its oxime and semicarbazone in concentrated H2SO4. ω-Bromonitro ketone and a series of 5-methyl-4-nitro-2-furyl-substituted azaheterocyclic compounds based on it were obtained.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. L. I. Belen'kii, I. B. Karmanova, G. P. Gromova, E. I. Novikova, Ya. L. Gol'dfarb, V. S. Bogdanov, and L. V. Shmelev,Zh. Org. Khim.,9, 1499 (1973).

    Google Scholar 

  2. N. O. Saldabol and S. A. Hiller,Chemistry of Heterocyclic Compounds. Pt. 2. Oxygen-containing Heterocycles [in Russian], Zinatne, Riga (1970), p. 118.

    Google Scholar 

  3. G. Rainier, German Patent Offen 261209,Chem. Abstr.,88, 6707 (1978).

    Google Scholar 

  4. K. Hayes and Ch. O'Keefe,J. Org. Chem.,19, 1897 (1954).

    Google Scholar 

  5. I. Rinkes,Rec. Trav. Chim.,50, 981 (1931).

    Google Scholar 

  6. N. O. Saldabol, V. A. Slavinskaya, Yu. Yu. Popelis, and I. B. Mazeika.Latv. Khim. Zhur. (in press).

  7. S. Gronowitz, I. Johnson, and A.-B. Hornfeldt,Chem. scripta,7, 211 (1975).

    Google Scholar 

  8. I. Rinkes,Rec. Trav. Chim.,49, 1118 (1930).

    Google Scholar 

  9. S. S. Mochalov, F. M. Abdel'razek, S. M. Gryaznov, T. P. Surikova, and Yu. S. Shabarov,Khim. Geterotsikl. Soedin., No. 7, 881 (1983).

    Google Scholar 

  10. N. O. Saldabol, V. A. Slavinskaya, Yu. Yu. Popelis, and I. B. Mazheika.Khim. Geterotsikl. Soedin., (in press).

  11. M. Hudlicky,Chem. Listy,51, 470 (1957).

    Google Scholar 

  12. E. E. Liepin'sh and N. O. Saldabol,Zh. Org. Khim.,17, 521 (1981).

    Google Scholar 

  13. N. O. Saldabol, E. E. Liepin'sh, Yu. Yu. Popelis, R. A. Gavar, L. Kh. Baumane, and I. S. Birgele,Zh. Org. Khim.,15, 2534 (1979).

    Google Scholar 

  14. G. Ocskay and L. Vargha,Tetrahedron,2, 140 (1958).

    Google Scholar 

Download references

Authors
  1. N. O. Saldabol
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Slavinskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. E. Liepinsh
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yu. Yu. Popelis
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. I. B. Mazheika
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Latvian Institute of Organic Synthesis, Riga LV-1006; e-mail: elmira@osi.lanet.lv. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1619–1626, December, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Saldabol, N.O., Slavinskaya, V.A., Liepinsh, E.E. et al. Synthesis and conversions of 2-acetyl-5-methyl-4-nitrofuran. Isomerization and beckman rearrangement of the oxime. Chem Heterocycl Compd 35, 1415–1422 (1999). https://doi.org/10.1007/BF02251814

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02251814

Keywords

Search

Navigation