Skip to main content
SpringerLink
Log in

Condensation of 3-Hydroxyimino-2-butanone Hydrazone with 2,4-Pentanedione, Isatin, Ethyl 2-Cyano-3-Ethoxyacrylate, and β-Ketoacid Esters and Anilides

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

Abstract

The condensation of 3-hydroxyimino-2-butanone hydrazone with 2,4-pentanediones yields 1,8-di-hydroxy-2,3,6-trimethyl-1,4,5-triaza-1,3,5,7-nonatetraene which exists in the iminoenol form. The reactionsof the title hydrazone with ethyl 2-cyano-3-ethoxyacrylate, ethyl acetoacetate, methyl 2-oxocyclopentane-carboxylate, acetoacetanilides occur in a regioselective fashion to afford the corresponfing enaminetautomers; isatin reacts at the 3-oxo group.

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. Valter, R.E., Kol'chato-tsepnaya izomeriya v organicheskoi khimii (Ring-Chain Isomerism in Organic Chemistry), Riga: Zinatne, 1978.

    Google Scholar 

  2. Fischer, R.H. and Weitz, H.M., Synthesis, 1975, no. 12, pp. 794-795.

  3. Kozhevnikov, D.N., Kozhevnikov, V.N., Rusinov, V.L., Chupakhin, O.N., Sidorov, E.O., and Klyuev, N.A., Russ. J. Org. Chem., 1998, vol. 34, no. 3, pp. 393-399.

    Google Scholar 

  4. Kitaev, Yu.P. and Buzykin, B.I., Gidrazony (Hydrazones), Moscow: Nauka, 1974, p. 48.

    Google Scholar 

  5. Bagrov, F.V., Zh. Obshch. Khim., 1989, vol. 59, no. 6, pp. 1320-1325.

    Google Scholar 

  6. Bagrov, F.V., Zh. Obshch. Khim., 1991, vol. 61, no. 4, pp. 886-889.

    Google Scholar 

  7. Bagrov, F.V., Zh. Obshch. Khim., 1992, vol. 62, no. 10, pp. 2262-2265.

    Google Scholar 

  8. Bagrov, F.V., Zh. Org. Khim., 1994, vol. 30, no. 5, pp. 741-743.

    Google Scholar 

  9. Bagrov, F.V., Russ. J. Org. Chem., 1997, vol. 33, no. 1, pp. 68-71.

    Google Scholar 

  10. Bagrov, F.V., Russ. J. Gen. Chem., 1995, vol. 65, no. 3, pp. 432-433.

    Google Scholar 

  11. Bagrov, F.V., Russ. J. Gen. Chem., 1998, vol. 68, no. 8, pp. 1217-1220.

    Google Scholar 

  12. Bagrov, F.V., Zh. Obshch. Khim., 1990, vol. 60, no. 5, pp. 1028-1033.

    Google Scholar 

  13. Bagrov, F.V. and Molchadskii, A.S., Zh. Org. Khim., 1992, vol. 28, no. 1, pp. 87-91.

    Google Scholar 

  14. Bagrov, F.V. and Orlov, V.N., Zh. Obshch. Khim., 1991, vol. 61, no. 1, pp. 92-96.

    Google Scholar 

  15. Bagrov, F.V. and Bagrov, D.F., Zh. Org. Khim., 1993, vol. 29, no. 11, pp. 2260-2263.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ul'yanov Chuvash State University, Moskovskii pr. 15, Cheboksary, 428015, Russia

    F. V. Bagrov

Authors
  1. F. V. Bagrov
    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

Bagrov, F.V. Condensation of 3-Hydroxyimino-2-butanone Hydrazone with 2,4-Pentanedione, Isatin, Ethyl 2-Cyano-3-Ethoxyacrylate, and β-Ketoacid Esters and Anilides. Russian Journal of Organic Chemistry 37, 15–19 (2001). https://doi.org/10.1023/A:1012352828786

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1012352828786

Keywords

Search

Navigation