Skip to main content
SpringerLink
Log in

Synthesis of (2-Ethoxy-2-oxoethylthio)methyl Derivatives of Furoic Acids and Attempts of Their Intramolecular Cyclizations under the Conditions of the Claisen Reaction

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

Abstract

Based on reactions of phosphorylated derivatives of halomethylfuroic acid esters with thioglycolic acid ester in the presence of bases, a method for the synthesis of mono-and bisphosphosphorylated esters of (2-ethoxy-2-oxoethylthio)methyl derivatives of furoic acids, containing an ester group in the position adjacent to the sulfide moiety was developed. Obtained compounds are relatively easily metallized with potassium tert-butylate, but intramolecular cyclization proceeds smoothly only in the case of 5-(diethoxyphosphorylmethyl)-2-(ethoxycarbonylmethylthiomethyl)furan-3-carboxylic acid. The resulting 1,3-dicarbonyl derivative of 7H-thiopyrano[3,4-b]furan is hydrolytically unstable, but its enol O-methyl ether is stabile. Alkaline hydrolysis of the latter compound was studied, and it was shown that it proceeds at the ester as well as at the phosphonate group.

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

Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme
Scheme

Similar content being viewed by others

REFERENCES

  1. Kawai, K., Chin, J., and Just, G., Nucleosides, Nucleotides, 1990, vol. 9, p. 1045. https://doi.org/10.1080/07328319008046061

    Article  CAS  Google Scholar 

  2. Subba Reddy, B.V., Venkateswarlu, A., Borkar, P., Yadav, J.S., Sridhar, B., and Gree, R., J. Org. Chem., 2014, vol. 79, p. 2716. https://doi.org/10.1021/jo402832t

    Article  CAS  Google Scholar 

  3. Schickmous, B. and Christoffers, J., Eur. J. Org. Chem., 2014, no. 20, p. 4410. https://doi.org/10.1002/ejoc201402388

    Article  Google Scholar 

  4. Kudo, N., Yoneda, A., Sato, K., Honma, T., and Sugai, T., Chem. Pharm. Bull., 2000, vol. 28, no. 4, p. 509. https://doi.org/10.1248/cpb.48.509

    Article  Google Scholar 

  5. Williams, D.R., Klingler, F.D., Allen, E.E., and Lichtenthaler, F.D., Tetrahedron Lett., 1988, vol. 29, p. 5087. https://doi.org/10.1016/s0040-4039(00)80686-3

    Article  CAS  Google Scholar 

  6. Pevzner, L.M., Russ. J. Gen. Chem., 2012, vol. 82, no. 12, p. 1938. https://doi.org/10.1134/S1070363212120067

    Article  CAS  Google Scholar 

  7. Pevzner, L.M., Russ. J. Gen. Chem., 2017, vol. 87, no. 7, p. 1516. https://doi.org/10.1134/S107036321707012X

    Article  CAS  Google Scholar 

  8. Pevzner, L.M., Russ. J. Gen. Chem., 2011, vol. 81, no. 1, p. 56. https://doi.org/10.1134/S1070363211010099

    Article  CAS  Google Scholar 

  9. Pevzner, L.M., Russ. J. Gen. Chem., 2012, vol. 82, no. 12, p. 1938. https://doi.org/10.1134/S107036321212006

    Article  CAS  Google Scholar 

Download references

Funding

The work was carried out within the frames of the basic part of the state project of the Ministry of Education and Science of Russia no. 4.5554.2017/8.9 using the equipment of the engineering center of the St. Petersburg State Technological Institute (Technical University).

Author information

Authors and Affiliations

  1. St. Petersburg Institute of Technology (Technical University), 190013, St. Petersburg, Russia

    L. M. Pevzner

  2. I.I. Mechnikov Northwestern State Medical University, 195067, St. Petersburg, Russia

    N. P. Stepanova

Authors
  1. L. M. Pevzner
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. P. Stepanova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. M. Pevzner.

Ethics declarations

No conflict of interest was declared by the authors.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pevzner, L.M., Stepanova, N.P. Synthesis of (2-Ethoxy-2-oxoethylthio)methyl Derivatives of Furoic Acids and Attempts of Their Intramolecular Cyclizations under the Conditions of the Claisen Reaction. Russ J Gen Chem 90, 166–181 (2020). https://doi.org/10.1134/S1070363220020024

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363220020024

Keywords:

Search

Navigation