Skip to main content
SpringerLink
Log in

Synthesis of Thiochroman 1,1-Dioxide Derivatives on the Basis of 2,4,6-Trinitrotoluene

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Treatment of 2,4,6-trinitrotoluene with β-mercaptocarboxylic acid esters and subsequent oxidation gave 2-(alkoxycarbonyl-R-methylsulfonyl)-4-X-6-nitrotoluenes which were brought into Knoevenagel condensation with aromatic aldehydes (heating in benzene in the presence of secondary amine acetates). As a result of intramolecular cyclization, 2-alkoxycarbonyl-3-aryl-2-R-5-X-7-nitrothiochroman 1,1-dioxides (R = H, Me; X = NO2, R'SO2) were obtained. The developed procedure opens the way to hitherto unknown thiochroman 1,1-dioxide derivatives.

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. Dutov, M.D., Serushkina, O.V., and Shevelev, S.A., Mendeleev Commun., 2002, p. 17.

  2. Tartakovsky, V.A., Shevelev, S.A., Dutov, M.D., Shakhnes, A.Kh., Rusanov, A.L., Komarova, L.G., and Andrievsky, A.M., Conversion Concepts for Commercial Applications and Disposal Technologies of Energetic Systems, Krause, H., Ed., Dordrecht: Kluwer Academic, 1997, p. 137.

    Google Scholar 

  3. Tartakovskii, V.A., Shevelev, S.A., and Rusanov, A.L., Abstracts of Papers, XVI Mendeleevskii s"ezd po obshchei i prikladnoi khimii (XVIth Mendeleev Congr. on General and Applied Chemistry), Moscow, 1998, part 2, p. 504.

  4. Shevelev, S.A., Tartakovsky, V.A., and Rusanov, A.L., Combustion of Energetic Materials, Kuo, K.K. and DeLuca, L.T., Eds., New York: Begell House, 2002, p. 62.

    Google Scholar 

  5. Serushkina, O.V., Dutov, M.D., and Shevelev, S.A., Russ. Chem. Bull., 2001, vol. 50, p. 261.

    Google Scholar 

  6. Serushkina, O.V., Dutov, M.D., Solkan, V.N., and Shevelev, S.A., Russ. Chem. Bull., 2001, vol. 50, p. 2406.

    Google Scholar 

  7. Rozhkov, V.V., Kuvshinov, A.M., and Shevelev, S.A., Synth. Commun., 2002, vol. 32, p. 1465.

    Google Scholar 

  8. Rozhkov, V.V., Kuvshinov, A.M., Gulevskaya, V.I., Chervin, I.I., and Shevelev, S.A., Synthesis, 1999, p. 2065.

Download references

Author information

Authors and Affiliations

  1. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    V. A. Tartakovskii, S. A. Shevelev, M. D. Dutov, O. V. Serushkina & V. V. Kachala

Authors
  1. V. A. Tartakovskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. A. Shevelev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. M. D. Dutov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. O. V. Serushkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. V. V. Kachala
    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

Tartakovskii, V.A., Shevelev, S.A., Dutov, M.D. et al. Synthesis of Thiochroman 1,1-Dioxide Derivatives on the Basis of 2,4,6-Trinitrotoluene. Russian Journal of Organic Chemistry 39, 397–402 (2003). https://doi.org/10.1023/A:1025597816012

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1025597816012

Keywords

Search

Navigation