Skip to main content
SpringerLink
Log in

Reaction of 4-diethylaminosalicylaldehyde with malononitrile

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The composition of the products from the reaction of 4-diethylaminosalicylaldehyde with malononitrile depends on the reaction conditions. A suitable method for the preparation of 2-dicyanomethylene-2H-1-benzopyrans is proposed. The dissociative ionization under electron impact of coumarin analogs has been studied. The relation between the polarity of the exocyclic double bond at C2 of coumarin, the position of the 1H NMR signal, and the position of the long-wavelength absorption band in the electronic spectrum is established.

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. I. I. Grandberg, L. K. Denisov, and O. A. Popova, Khim. Geterotsikl. Soedin., No. 2, 147 (1987).

    Google Scholar 

  2. B. M. Krasovitskii and B. M. Bolotin, Organic Luminophores [in Russian], Khimiya, Moscow (1984), p. 145.

    Google Scholar 

  3. M. B. Levin, Z. V. Todres, and A. S. Cherkasov, Kvant. Élektron., 13, No. 7, 1409 (1986).

    Google Scholar 

  4. V. V. Maslov, M. I. Dzyubenko, and V. M. Nikitchenko, Kvant. Élektron., 16, No. 4, 709 (1989).

    Google Scholar 

  5. G. P. Schiemenz, Chem. Ber., 95, 483 (1962).

    Google Scholar 

  6. L. L. Woods and J. Sapp, J. Org. Chem., 30, No. 1, 312 (1965).

    Google Scholar 

  7. Kakenyako Kako Co., Japanese Patent No. 81,152,471; Chem. Abstr., 96, 122,636 (1982).

    Google Scholar 

  8. K. Sato, Japanese Patent No. 7,394,727; Chem. Abstr., 80, 122,417 (1974).

    Google Scholar 

  9. P. Czerney and H. Hartmann, J. Prakt. Chem., 323, No. 4, 691 (1981).

    Google Scholar 

  10. H. Junek, Monatsh. Chem., 94, No. 1, 192 (1963).

    Google Scholar 

  11. S. Abdou, S. M. Fahmy, M. M. Khader, and M. H. Elnagdi, Monatsh. Chem., 113, No. 8–9, 985 (1982).

    Google Scholar 

  12. H. Junek, Monatsh. Chem., 95, No. 1, 234 (1964).

    Google Scholar 

  13. F. Freedman, Chem. Rev., 69, No. 5, 591 (1969).

    Google Scholar 

  14. H. Junek, Monatsh. Chem., 93, No. 3, 684 (1962).

    Google Scholar 

  15. G. Renzi, P. Mascagni, and E. I. Piumelli, Boll. Chim. Pharm., 120, No. 9, 525 (1981).

    Google Scholar 

  16. J. F. Roudier and A. Foucard, Synthesis, No. 2, 159 (1984).

    Google Scholar 

  17. A. V. Reznichenko, I. I. Tkach, and E. A. Luk'yanets, in: Abstracts, 4th All-Union Conference on Organic Luminophores and Their Use in the National Economy, Khar'kov (1984), p. 137.

  18. A. J. Fatiadi, Synthesis, No. 3, 165 (1978).

    Google Scholar 

  19. S. K. Gorozhankin, M. A. Kiprichenok, N. A. Klyuev, and I. I. Grandberg, Izv. TSKhA, No. 4, 151 (1986).

    Google Scholar 

  20. N. A. Klyuev, S. K. Gorozhankin, M. A. Kiprichenok, and I. I. Grandberg, Izv. TSKhA, No. 4, 159 (1989).

    Google Scholar 

  21. M. A. Kiprichenok, I. I. Grandberg, L. K. Denisov, and L. M. Mel'nikova, Izv. TSKhA, No. 3, 172 (1985).

    Google Scholar 

  22. P. Czerney and H. Hartmann, J. Prakt. Chem., 324, No. 1, 21 (1982).

    Google Scholar 

  23. M. L. Sassiver and J. H. Boothe, US Patent No. 4,317,774; Chem. Abstr., 97, 23532 (1982).

    Google Scholar 

  24. M. A. Kiprichenok, S. K. Gorozhankin, and I. I. Grandberg, Khim. Geterotsikl. Soedin., No. 6, 751 (1988).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Research Institute for Organic Intermediates and Dyestuffs, 103787, Moscow

    I. I. Tkach, A. V. Reznichenko & E. A. Luk'yanets

Authors
  1. I. I. Tkach
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. V. Reznichenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. A. Luk'yanets
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1043–1052, August, 1992.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Tkach, I.I., Reznichenko, A.V. & Luk'yanets, E.A. Reaction of 4-diethylaminosalicylaldehyde with malononitrile. Chem Heterocycl Compd 28, 872–880 (1992). https://doi.org/10.1007/BF00531317

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00531317

Keywords

Search

Navigation