Skip to main content
SpringerLink
Log in

A new stereoselective synthesis of 2-amino-4,5-dihydrothiophene-3-carbonitrile derivatives

  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A new stereoselective method for the synthesis of trans-isomers of 2-amino-4-aryl-5-benzoyl-4,5-dihydrothiophene-3-carbonitriles was proposed. The method involves base-catalyzed reactions of phenacyl thiocyanate with 3-(het)aryl-2-cyanoprop-2-enethioamides. (4R,5S/4S,5R)-2-Amino-5-benzoyl-4-(2-chlorophenyl)-4,5-ihydrothiophene-3-carbonitrile was structurally characterized by X-ray diffraction analysis.

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. K. Gewald, Khim. Geterotsikl. Soedin., 1976, 1299 [Chem. Heterocycl. Compd., 1976, 12, 1077 (Engl. Transl.)].

  2. F. S. Babichev, Yu. A. Sharanin, V. P. Litvinov, V. K. Promonenkov, and Yu. M. Volovenko, Vnutrimolekulyarnoe vzaimodeistvie nitril’noi i S-N-, O-N-i S-H-grupp [Intramolecular Interactions of Cyano and S-N, O-N, and S-H Groups], Naukova Dumka, Kiev, 1985, 200 pp. (in Russian).

    Google Scholar 

  3. R. W. Sabnis, D. W. Rangnekar, and N. D. Sonawane, J. Heterocycl. Chem., 1999, 36, 333.

    Article  CAS  Google Scholar 

  4. V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2004, 463 [Russ. Chem. Bull., Int. Ed., 2004, 53, 487].

  5. V. P. Litvinov, V. V. Dotsenko, and S. G. Krivokolysko, Izv. Akad. Nauk, Ser. Khim., 2005, 847 [Russ. Chem. Bull., Int. Ed., 2005, 54, 864].

    Google Scholar 

  6. E. A.-G. Bakhite, Phosphorus, Sulfur, Silicon, Relat. Elem., 2003, 178, 929.

    Article  CAS  Google Scholar 

  7. H. Maruoka, K. Yamagata, and M. Yamazaki, Liebigs Ann. Chem., 1993, 1269; H. Maruoka, M. Yamazaki, and Y. Tomioka, J. Heterocycl. Chem., 2004, 41, 641.

  8. H. Maruoka, F. Yamagata, and M. Yamazaki, J. Heterocycl. Chem., 2001, 38, 269.

    CAS  Google Scholar 

  9. A. M. Shestopalov, D. Sc. (Chem.) Thesis, IOKh AN SSSR, Moscow, 1991 (in Russian).

  10. L. A. Rodinovskaya, D. Sc. (Chem.) Thesis, IOKh RAN, Moscow, 1994 (in Russian).

  11. A. M. Shestopalov, O. P. Bogomolova, L. A. Rodinovskaya, V. P. Litvinov, and Yu. A. Sharanin, Dokl. Akad. Nauk SSSR, 1991, 317, 112 [Dokl. Chem., 1991, 317 (Engl. Transl.)].

    CAS  Google Scholar 

  12. L. A. Rodinovskaya, A. M. Shestopalov, and V. P. Litvinov, Dokl. Akad. Nauk, 1994, 339, 214 [Dokl. Chem., 1994, 339 (Engl. Transl.)].

    CAS  Google Scholar 

  13. A. M. Shestopalov, O. P. Bogomolova, and V. P. Litvinov, Synthesis, 1991, 277.

  14. K. M. Dawood, Synth. Commun., 2001, 31, 1647.

    Article  CAS  Google Scholar 

  15. A. V. Samet, A. M. Shestopalov, V. N. Nesterov, and V. V. Semenov, Synthesis, 1997, 623.

  16. A. V. Samet, A. M. Shestopalov, V. N. Nesterov, and V. V. Semenov, Izv. Akad. Nauk, Ser. Khim., 1998, 127 [Russ. Chem. Bull., 1998, 47, 127 (Engl. Transl.)].

    Google Scholar 

  17. V. P. Litvinov, Usp. Khim., 1999, 68, 817 [Russ. Chem. Rev., 1999, 68, 737 (Engl. Transl.)].

    Google Scholar 

  18. A. M. Shestopalov and K. G. Nikishin, Khim. Geterotsikl. Soedin., 1998, 1267 [Chem. Heterocycl. Compd., 1998, 34 (Engl. Transl.)].

  19. V. V. Dotsenko, Ph.D. (Chem.) Thesis, IOKh RAN, Moscow, 2004 (in Russian).

  20. N. N. Mel’nikov and N. D. Sukhareva, in Reaktsii i metody issledovaniya organicheskikh soedinenii [Reactions and Methods of Investigations of Organic Compounds], Vol. 8, Eds V. M. Rodionov, B. A. Kazanskii, I. L. Knunyants, M. M. Shemyakin, and N. N. Mel’nikov, Goskhimizdat, Moscow, 1959, p. 9 (in Russian).

    Google Scholar 

  21. R. H. Wiley, D. C. England, and L. C. Behr, Organic Reactions, Vol. 6, Ed. R. Adams, John Wiley and Sons, New York, 1951; G. Vernin, in Thiazole and Its Derivatives. The Chemistry of Heterocyclic Compounds, Vol. 34, P. 1, Ed. J. V. Metzger, John Wiley and Sons, New York, 1979, p. 271.

    Google Scholar 

  22. A. Matsubara, K. Sakai, H. Tanada, A. Mizuchi, K. Horikomi, and T. Ohtsu, US Pat. 5 112 841 (1992); http://patft.uspto.gov/netahtml/srchnum.htm.

  23. S. Guenter, US Pat. 4 371 734; Chem. Abstrs, 1983, 98, 198202g.

    Google Scholar 

  24. S. Günter, FRG Application 2 801 794 (1979); http://ep.espacenet.com.

  25. H. K. Gakhar, A. Madan, and N. Kumar, Indian J. Chem., Sect. B, 1980, 19, 250.

    Google Scholar 

  26. A. M. Salah El-Din, Sulfur Lett., 2003, 26, 35.

    Article  CAS  Google Scholar 

  27. F. M. Abdelrazek, N. S. Ibrahim, Z. E.-S. Kandeel, and M. H. Elnagdi, Synthesis, 1984, 970.

  28. A. Fava, A. Iliceto, and A. Ceccon, Tetrahedron Lett., 1963, 4, 685.

    Article  Google Scholar 

  29. A. Ceccon, I. Papa, and A. Fava, J. Am. Chem. Soc., 1966, 88, 4643.

    Article  CAS  Google Scholar 

  30. S. I. Al-Khalil and W. R. Bowman, Tetrahedron Lett., 1983, 24, 2517.

    Article  CAS  Google Scholar 

  31. M. Burke-Laing and M. Laing, Acta Crystallogr., Sect. B, 1976, 32, 3216.

    Article  Google Scholar 

  32. F. H. Allen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpen, and R. Tailor, J. Chem. Soc., Perkin Trans. 2, 1987, 12, S1.

  33. L. N. Kuleshova and P. M. Zorkii, Acta Crystallogr., Sect. B, 1981, 37, 1363.

    Article  Google Scholar 

  34. J. S. A. Brunskill, A. De, and D. F. Ewing, J. Chem. Soc., Perkin Trans. 1, 1978, 629.

  35. D. J. Watkin, C. K. Prout, J. R. Carruthers, and P. W. Betteridge, CRYSTALS, Issue 10, Chemical Crystallography Laboratory, University of Oxford, 1996.

  36. J. R. Carruthers and D. J. Watkin, Acta Crystallogr., Sect. A, 1979, 35, 698.

    Article  Google Scholar 

  37. A. C. T. North, D. C. Phillips, F. Scott, and F. S. Mathews, Acta Crystallogr., Sect. A, 1968, 24, 351.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. ChemEx Laboratory, V. Dal’ East-Ukrainian National University, 20a Molodyozhny kv., 91034, Lugansk, Ukraine

    V. V. Dotsenko & S. G. Krivokolysko

  2. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 ul. Murmanskaya, 02094, Kiev, Ukraine

    A. N. Chernega

  3. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. P. Litvinov

Authors
  1. V. V. Dotsenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. G. Krivokolysko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. N. Chernega
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. P. Litvinov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. V. Dotsenko.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1379–1383, July, 2007.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dotsenko, V.V., Krivokolysko, S.G., Chernega, A.N. et al. A new stereoselective synthesis of 2-amino-4,5-dihydrothiophene-3-carbonitrile derivatives. Russ Chem Bull 56, 1431–1436 (2007). https://doi.org/10.1007/s11172-007-0217-7

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-007-0217-7

Key words

Search

Navigation