Skip to main content
SpringerLink
Log in

Quantum-chemical Modeling of the Reaction of 3-Pyridinecarbaldehyde with 3-Cyano-4,5,5-trimethyl-2(5H)-furanone

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The condensation of pyridinecarbaldehydes with 3-cyano-4,5,5-trimethyl-2(5H)-furanone and 3-cyano-4,6,6-trimethyl-5,6-dihydro-2(2H)-pyranone leads to the formation of the products of crotonic condensation and compounds of the Michael adduct type. A model investigation of the mechanism by the semiempirical AM1 quantum-chemical method for the case of the reaction of 3-pyridinecarbaldehyde with 3-cyano-4,5,5-trimethyl-2(5H)-furanone showed that the products can be formed in parallel from one and the same intermediate compound.

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. C. S. Marvel, L. E. Coleman, and G. P. Scott, J. Org. Chem., 20, 1785 (1955).

    Google Scholar 

  2. S. V. Tsukerman, K.-S. Chang, and V. F. Lavrushin, 34, 832 (1964).

    Google Scholar 

  3. N. Wachter-Jurcsak, C. Radu, and K. Redin, Tetrahedron Lett., 39, 3903 (1998).

    Google Scholar 

  4. D. Jansone, L. Leite, M. Fleisher, Yu. Popelis, I. Mazheika, E. Lukevics, F. Melikyan, and A. Avetisyan, Khim. Geterotsikl. Soedin., 298 (1998).

  5. J. March, Advanced Organic Chemistry: Reactions, Mechanisms and Structures, 4th Edn., New York (1992).

  6. F. A. Alien, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Taylor, J. Chem. Soc. Perkin Trans. 2, No. 12, S1 (1987).

  7. C. K. Ingold, Theoretical Principles of Organic Chemistry[Russian translation], Mir, Moscow (1973).

    Google Scholar 

  8. J. J. P. Stewart, Program package MOPAC (QCPE N 455). Version 5.0.

  9. D. F. Shanno and J. Optimiz, Theory Appl., 46, 87 (1985).

    Google Scholar 

  10. J. J. P. Stewart, Program package MOPAC. Manual, Chap. 6.

  11. LabVision (Version 1,1992), TRIPOS Associates Inc., 1699 S. Hanley Rd., St. Louis, MO, 63144, USA.

Download references

Author information

Authors and Affiliations

  1. Latvian Institute of Organic Synthesis, Riga

    M. Fleisher, D. Jansone, G. Andreeva, L. Leite & E. Lukevics

Authors
  1. M. Fleisher
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. Jansone
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. Andreeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. L. Leite
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. Lukevics
    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

Fleisher, M., Jansone, D., Andreeva, G. et al. Quantum-chemical Modeling of the Reaction of 3-Pyridinecarbaldehyde with 3-Cyano-4,5,5-trimethyl-2(5H)-furanone. Chemistry of Heterocyclic Compounds 37, 688–693 (2001). https://doi.org/10.1023/A:1011905026968

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1011905026968

Search

Navigation