Skip to main content
Log in

A new method for the synthesis of esters of β-thiophenecarboxylic acids

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A method for the synthesis of esters of β-thiophenecarboxylic acids and diethyl 3-methyl-2,4-thiophenedicarboxylate by the deamination of derivatives of 2-amino-3-ethoxycarbonylthiophene has been proposed. Ethyl tetrahydrothionaphthene-3-carboxylate has been converted by dehydrogenation on heating with sulfur into ethyl thionaphthene-3-carboxylic acid. The corresponding acids have been obtained by the hydrolysis of the esters. A number of dialkylaminoalkyl esters has been obtained from β-thiophenecarboxylic acids and 3-methyl-2, 4-thiophenedicarboxylic acid via the acid chlorides.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. H. D. Hartough, Thiophene and its Derivatives, N. Y., 105, 363, 1952.

    Google Scholar 

  2. F. Muhlert, Ber., 18, 3003, 1885.

    Google Scholar 

  3. A. Damsky, Ber., 19, 3282, 1886.

    Google Scholar 

  4. M. G. L. Voermann, Rec. trav. chim., 26, 293, 1907.

    Google Scholar 

  5. E. Campaigne and W. M. LeSuer, J. Am. Chem. Soc, 70, 1555, 1948.

    Google Scholar 

  6. I. J. Rinkes, Rec. trav. chim., 55, 991, 1936.

    Google Scholar 

  7. S. Nishimura, R. Motoyama, and E. Imoto, Bull. Univ. Osaka Prefect., Ser. A. 6, 127, 1958; C. A., 53, 4249, 1959.

    Google Scholar 

  8. W. Steinkopf and W. Hanske, Ann., 527, 264, 1936.

    Google Scholar 

  9. W. Steinkopf and W. Hanske, Ann., 532, 236, 1937.

    Google Scholar 

  10. W. Steinkopf and H. F. Smitt, Ann., 533, 264, 1938.

    Google Scholar 

  11. R. Gaerther, J. Am. Chem. Soc., 72, 4326, 1950.

    Google Scholar 

  12. R. Gaerther, J. Am. Chem. Soc, 73, 3934, 1951.

    Google Scholar 

  13. V. I. Shvedov, R. K. Ryzhkova, and A. N. Grinev, Authors' Certificate 187801; Byull. izobr., No. 21, 43, 1966.

    Google Scholar 

  14. K. Gewald, Z. Chem., 2, 305, 1962; C. A. 58, 6770, 1963.

    Google Scholar 

  15. V. I. Shvedov and A. N. Grinev, ZhOrKh, 1, 2228, 1965.

    Google Scholar 

  16. V. I. Shvedov, V. K. Ryzhkova, and A. N. Grinev, KhGS [Chemistry of Heterocyclic Compounds], 239, 1967.

  17. V. I. Shvedov, V. K. Ryzhkova, and A. N. Grinev, KhGS [Chemistry of Heterocyclic Compounds], 450, 1967.

  18. K. Gewald, Chem. Ber., 98, 3571, 1965.

    Google Scholar 

  19. K. Gewald, E. Schinke, and H. Bottcher, Chem. Ber., 99, 94, 1966.

    Google Scholar 

  20. E. R. Atkinson, D. Holm-Hansen, A. D. Nevers, and S. A. Marino, J. Am. Chem. Soc., 65, 476, 1943.

    Google Scholar 

  21. L. F. Fieser and R. G. Kennelly, J. Am. Chem. Soc., 57, 1611, 1935.

    Google Scholar 

  22. A. W. Horton, J. Org. Chem., 14, 760, 1949.

    Google Scholar 

  23. G. Komppa, J. pr. Chem., 122, 331, 1929.

    Google Scholar 

  24. G. Komppa, J. pr. Chem., 138, 116, 1933.

    Google Scholar 

  25. M. Yamaguchi, IR Spectra, 4, 85, 1958.

    Google Scholar 

  26. M. Yamaguchi, Japan Analyst, 4, 210, 1958.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shvedov, V.I., Ryzhkova, V.K. & Grinev, A.N. A new method for the synthesis of esters of β-thiophenecarboxylic acids. Chem Heterocycl Compd 3, 789–792 (1967). https://doi.org/10.1007/BF00474869

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00474869

Navigation