Skip to main content
SpringerLink
Log in

Five-Membered 2,3-Dioxo Heterocycles: XLVII. Reaction of 5-Aryl-4-phenyl-2,3-dihydrofuran-2,3-diones with Compounds Containing C = N and C≡N Bonds

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Thermal decarbonylation of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones gives rise to intermediate aroyl(phenyl)ketenes which react with nonactivated Schiff bases, N,N'-dicyclohexylcarbodiimide, and p-di-methylaminobenzonitrile according to the [4 + 2]-cycloaddition pattern with formation of 6-aryl-5-phenyl-4H-1,3-oxazin-4-ones. Reactions of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones with activated Schiff bases at a temperature below the thermolysis temperature lead to 4-aroyl-4-phenyltetrahydropyrrole-2,3-diones.

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. Lisovenko, N.Yu., Maslivets, A.N., and Aliev, Z.G., Russ. J. Org. Chem., 2004, vol. 40, p. 1053.

    Google Scholar 

  2. Andreichikov, Yu.S., Koz'minykh, O.V., Ionov, Yu.V., and Saraeva, R.F., Khim. Geterotsikl. Soedin., 1978, p. 271.

  3. Andreichikov, Yu.S. and Ionov, Yu.V., Zh. Org. Khim., 1982, vol. 18, p. 2430.

    Google Scholar 

  4. Karpova, L.N., Kolotova, N.V., Shurov, S.N., and Andreichikov, Yu.S., Zh. Org. Khim., 1992, vol. 28, p. 779.

    Google Scholar 

  5. Andreichikov, Yu.S. and Shurov, S.N., Zh. Org. Khim., 1983, vol. 19, p. 1983.

    Google Scholar 

  6. Andreichikov, Yu.S., Nekrasov, D.D., Rudenko, M.A., and Konovalov, A.Yu., Khim. Geterotsikl. Soedin., 1987, p. 740.

  7. Andreichikov, Yu.S., Maslivets, A.N., and Ivanenko, O.I., Zh. Org. Khim., 1986, vol. 22, p. 1790.

    Google Scholar 

  8. Vostrov, E.S., Lisovenko, N.Yu., Tarasova, O.P., and Maslivets, A.N., Khim. Geterotsikl. Soedin., 2001, p. 1282.

  9. Fieser, L.F. and Fieser, M., Reagents for Organic Synthesis, New York: Wiley, 1968, vol. 1. Translated under the title Reagenty dlya organicheskogo sinteza, Moscow: Mir, 1970, vol. 1, p. 239.

    Google Scholar 

Download references

Authors
  1. E. S. Vostrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. V. Leont'eva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. P. Tarasova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. N. Maslivets
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vostrov, E.S., Leont'eva, E.V., Tarasova, O.P. et al. Five-Membered 2,3-Dioxo Heterocycles: XLVII. Reaction of 5-Aryl-4-phenyl-2,3-dihydrofuran-2,3-diones with Compounds Containing C = N and C≡N Bonds. Russian Journal of Organic Chemistry 40, 1058–1061 (2004). https://doi.org/10.1023/B:RUJO.0000045204.07277.72

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/B:RUJO.0000045204.07277.72

Keywords

Search

Navigation