Skip to main content
Log in

Stereoselective Synthesis and Alkylation of N-Methylmorpholinium 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-5-(2-thenoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine-2-thiolate. Molecular and Crystal Structure of 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-2-methallylthio-5-(2-thenoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The condensation of 2-chlorobenzaldehyde with cyanothioacetamide and 2-thenoyltrifluoroacetone in the presence of N-methylmorpholine takes place stereoselectively and leads to the formation of N-methylmorpholinium 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-5-(2-thenoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine-2-thiolate. The latter was used to synthesize the corresponding 2-alkylthiotetrahydropyridines. The structure of 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-2-methallylthio-5-(2-thenoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine was determined by X-ray crystallographic analysis.

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.

Institutional subscriptions

Similar content being viewed by others

REFERENCES

  1. V. P. Litvinov andV. D. Dyachenko, Dokl. Akad. Nauk, 352, 636 (1997).

    Google Scholar 

  2. V. P. Litvinov, Izv. Akad. Nauk, Ser. Khim., 2123 (1998).

  3. A. N. Vereshchagin, Usp. Khim., 52, 1879 (1983).

    Google Scholar 

  4. S. G. Krivokolysko,V. D. Dyachenko,E. B. Rusanov, andV. B. Litvinov, Khim. Geterotsikl. Soedin., 1076 (2001).

  5. R. W. Alder,N. C. Goode,T. J. King,J. M. Mellor, andB. W. Miller, J. Chem. Soc. Chem. Commun., 5, 173 (1976).

    Google Scholar 

  6. M. Burke-Laing andM. Laing, Acta Crystallogr. (B), 32, 3216 (1976).

    Google Scholar 

  7. P. Gilli,V. Bertolasi,V. Ferretti, andG. Gilli, J. Am. Chem. Soc., 116, 909 (1994).

    Google Scholar 

  8. L. N. Kuleshova andP. M. Zorkii, Acta crystallogr. (B), 37, 1363 (1981).

    Google Scholar 

  9. D. J. Watkin,C. K. Prout,J. R. Carruthers, andP. W. Betteridge, Crystals, Issue 10, Chemical Crystallography Laboratory, University of Oxford (1996).

  10. A. C. T. North,D. C. Phillips,F. Scott, andF. S. Mathews, Acta crystallogr. (A), 24, 351 (1968).

    Google Scholar 

  11. J. R. Carruthers andD. J. Watkin, Acta crystallogr. (A), 35, 698 (1979).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Krivokolysko, S.G., Dyachenko, V.D., Chernega, A.N. et al. Stereoselective Synthesis and Alkylation of N-Methylmorpholinium 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-5-(2-thenoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine-2-thiolate. Molecular and Crystal Structure of 4,5-trans-4-(2-chlorophenyl)-3-cyano-6-hydroxy-2-methallylthio-5-(2-thenoyl)-6-trifluoromethyl-1,4,5,6-tetrahydropyridine. Chemistry of Heterocyclic Compounds 37, 1208–1215 (2001). https://doi.org/10.1023/A:1013889208646

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1013889208646

Navigation