Skip to main content
SpringerLink
Log in

Regiospecific synthesis of 2-substituted 4-methyl-3,6-dihydro-2H-pyrans

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The chloroalkylation of 3-halo-2-methyl-1-buten-4-ols was used to synthesize 4,5-dihalo-4-methyl-2-substituted tetrahydropyrans, which were converted regiospecifically to 3,6-dihydropyrans by reaction with magnesium. A similar reaction with zinc dust gave mixtures of 3,6- and 5,6-dihydropyrans.

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

Literature cited

  1. Houben-Weyl, Methoden der Organischen Chemie, Vol. VI/4, Georg Thieme Verlag, Stuttgart (1966), p. 90.

    Google Scholar 

  2. A. A. Gevorkyan, Doctoral Dissertation, Yerevan (1978).

  3. A. A. Gevorkyan, G. G. Tokmadzhyan, S. M. Kosyan, and A. S. Arakelyan, Arm. Khim. Zh., 29, 278 (1976).

    Google Scholar 

  4. A. A. Gevorkyan and G. G. Tokmadzhyan, Arm. Khim. Zh., 29, 888 (1976).

    Google Scholar 

  5. A. A. Gevorkyan and A. S. Arakelyan, Arm. Khim. Zh., 29, 1033 (1976).

    Google Scholar 

  6. D. L. Rakhmankulov, R. A. Karakhanov, S. S. Zlotskii, V. A. Kantor, U. B. Imashev, and A. M. Svernin, The Chemistry and Technology of 1,3-Dioxacyclanes [in Russian], All-Union Institute of Scientific and Technical Information, Moscow (1979).

    Google Scholar 

  7. A. A. Gevorkyan, P. I. Kazaryan, O. V. Avakyan, and G. A. Panosyan, Arm. Khim. Zh., 37, 24 (1984).

    Google Scholar 

  8. P. I. Kazaryan, Master's Dissertation, Yerevan (1974).

  9. T. T. Minasyan and Sh. O. Badanyan, Arm. Khim. Zh., 32, 542 (1979).

    Google Scholar 

  10. G. Cainelli, G. Cardillo, M. Orena, and S. Sandri, J. Am. Chem. Soc., 98, 6737 (1976).

    Google Scholar 

  11. E. Y. Corey and J. W. Suggs, Tetrahedron Lett., No. 31, 2647 (1975).

    Google Scholar 

  12. A. A. Gevorkyan, P. I. Kazaryan, and S. V. Avakyan, Khim. Geterotsikl. Soedin., No. 1, 125 (1983).

    Google Scholar 

  13. A. A. Gevorkyan, N. M. Khizantsyan, P. I. Kazaryan, and G. A. Panosyan, Khim. Geterotsikl. Soedin., No. 2, 167 (1981).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, Academy of Sciences of the Armenian SSR, 375094, Yerevan

    P. I. Kazaryan, O. V. Avakyan, S. V. Avakyan & A. A. Gevorkyan

Authors
  1. P. I. Kazaryan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. V. Avakyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. V. Avakyan
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. A. Gevorkyan
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1189–1193, September, 1985.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kazaryan, P.I., Avakyan, O.V., Avakyan, S.V. et al. Regiospecific synthesis of 2-substituted 4-methyl-3,6-dihydro-2H-pyrans. Chem Heterocycl Compd 21, 988–992 (1985). https://doi.org/10.1007/BF00515020

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00515020

Keywords

Search

Navigation