Skip to main content
SpringerLink
Log in

Reactions of 2,2,4-trimethyl-1,2-dihydroquinoline and its derivatives with hexafluoroacetone and methyl trifluoropyruvate

  • Brief Communications
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The alkylation of 2,2,4-trimethyl-1,2-dihydroquinoline and its derivatives by hexafluoroacetone occurs regioselectively and leads, depending on the conditions, to 6-(2-hydroxyhexafluoro-2-propyl)-2,2,4-trimethyl-1,2-dihydroquinolines or the 6,8-disubstituted products.

  2. 2.

    The reaction of methyl trifluoropyruvate with 2,2,4-trimethyl-1,2-dihydroquinoline gave the product of C8-alkylation, accompanied by lactamization.

  3. 3.

    The oxidation of 6-(2-hyhdroxyhexafluoro-2-propyl)-2,2,4-trimethyl-1,2-dihydroquinoline by hydrogen peroxide in the presence of sodium tungstenate gave a stable nitroxyl radical.

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

Literature cited

  1. A. E. Zelenin, N. D. Chkanikov, A. M. Umnov, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2074 (1986).

    Google Scholar 

  2. M. S. Zhedek, O. N. Kucherenko, É. G. Rozantsev, and A. B. Shapiro, Zh. Prikl. Khim.,44, 2599 (1971).

    Google Scholar 

  3. É. V. Alekseev, A. B. Gagarina, L. A. Vakulova, et al., Izv. Akad. Nauk SSSR, Ser. Khim., 312 (1972).

  4. L. J. Machlin, R. S. Gordon, and K. H. Hasky, J. Nutrition,67, 333 (1959).

    Google Scholar 

  5. A. E. Zelenin, N. D. Chkanikov, A. F. Kolomiets, and A. V. Fokin, Izv. Akad. Nauk SSSR, Ser. Khim., No. 9, 2080 (1986).

    Google Scholar 

  6. A. R. Forrester and S. P. Hepburn, J. Chem. Soc., Perkin Trans, 1,19, 2208 (1974).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    K. V. Komarov, N. D. Chkanikov, V. I. Suskina, A. B. Shapiro, A. F. Kolomiets & A. V. Fokin

Authors
  1. K. V. Komarov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. D. Chkanikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. I. Suskina
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. B. Shapiro
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. F. Kolomiets
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. A. V. Fokin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 472–475, February, 1989.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Komarov, K.V., Chkanikov, N.D., Suskina, V.I. et al. Reactions of 2,2,4-trimethyl-1,2-dihydroquinoline and its derivatives with hexafluoroacetone and methyl trifluoropyruvate. Russ Chem Bull 38, 415–417 (1989). https://doi.org/10.1007/BF00953643

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00953643

Keywords

Search

Navigation