Skip to main content
SpringerLink
Log in

Acetals of lactams and amides. 60. N- and O-alkylation of 5-oxo-5,6,7,8-tetrahydrocarbostyryils. Synthesis of isoxazolo[5,4-f]- and pyrazolo[3,4-f]quinolines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The alkylation of 5-oxo-5,6,7,8-tetrahydrocarbostyrils has been examined by GLC. It has been found that, irrespective of the reaction conditions and the alkylating agent used, both N- and O-alkylation occur. When triethyloxonium fluoroborate and N,N-DMF diethyl acetal are used O-alkylation predominates, and with alkyl halides, N-alkylation. Reaction of N-ethyl-5-oxo-5,6,7,8-tetrahydrocarbostyril and 2-ethoxy-5-oxo-5,6,7,8-tetrahydrotetrahydroquinoline with DMF diethyl acetal gives the 6-dimethylaminomethylene derivatives, treatment of which with hydrazine hydrate or hydroxylamine affording isoxazolo[5,4-f]- or pyrazolo[3,4-f]quinolines.

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. T. I. Mukhanova, L. M. Alekseeva, and V. G. Granik,Khim. Geterotsikl. Soedin., No. 7, 888 (1990).

    Google Scholar 

  2. V. G. Granik, A. K. Shanazarov, N. P. Solov'eva, V. V. Chistyakov, I. V. Persianova, and Yu. N. Sheinker,Khim. Geterotsikl. Soedin., No. 11, 1470 (1987).

    Google Scholar 

  3. A. K. Shanazarov, N. P. Solov'eva, V. V. Chistyakov, Yu. N. Sheinker, and V. G. Granik,Khim. Geterotsikl. Soedin., No. 11, 1477 (1987).

    Google Scholar 

  4. A. Rocdig, R. Manger, and S. Schödel,Chem. Ber.,93, 2294 (1960).

    Google Scholar 

  5. L. T. Guss, L. V. Ershov, G. A. Bogdanova, and V. G. Granik,Khim. Geterotsikl. Soedin., No. 2, 215 (1990).

    Google Scholar 

  6. V. G. Granik, B. M. Pyatin, and V. G. Glushkov,Usp. Khim.,40, 1593 (1971).

    Google Scholar 

  7. M. A. T. Dubas-Sluyter, W. N. Speckamp, and H. O. Huirmann,Rec. Trav. Chim.,91, 157 (1972).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. S. Ordzhonikidze All-Union Research Institute for Pharmaceutical Chemistry, 119815, Moscow

    A. K. Shanazarov, V. A. Kuzovkin, V. V. Chistyakov & V. G. Granik

Authors
  1. A. K. Shanazarov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Kuzovkin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. V. Chistyakov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. G. Granik
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For Communication 59, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 86–92, January, 1991.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shanazarov, A.K., Kuzovkin, V.A., Chistyakov, V.V. et al. Acetals of lactams and amides. 60. N- and O-alkylation of 5-oxo-5,6,7,8-tetrahydrocarbostyryils. Synthesis of isoxazolo[5,4-f]- and pyrazolo[3,4-f]quinolines. Chem Heterocycl Compd 27, 71–76 (1991). https://doi.org/10.1007/BF00633222

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00633222

Keywords

Search

Navigation