Skip to main content
Log in

Addition of thiiranes to δ1-piperideines and δ1-pyrrolines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 2,3,4,5-tetrahydropyridines and 1-pyrrolines with thiiranes, which leads to perhydrothiazolo[2,3-a]pyridines and perhydropyrrolo[2,1-b]thiazoles, is described. The regiospecificity and stereoselectivity of the reaction are examined.

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.

Similar content being viewed by others

Literature cited

  1. V. V. Sokolov, K. A. Ogloblin, and A. A. Potekhin, Khim. Geterotsikl. Soedin., No. 5, 627 (1982).

    Google Scholar 

  2. F. Yu. Rachinskii and N. M. Slavachevskaya, The Chemistry of Amino Thiols [in Russian], Khimiya, Moscow-Leningrad (1965).

    Google Scholar 

  3. P. M. R. Barkworth and T. A. Crabb, J. Chem. Soc., Perkin Trans. II, No. 1, 91 (1982).

    Google Scholar 

  4. D. Barbry, D. Couturier, and G. Ricart, Synthesis, No. 5, 387 (1980).

    Google Scholar 

  5. S. W. Pelletier, J. Nowacki, and N. W. Mody, Synth. Commun., 9, 201 (1979).

    Google Scholar 

  6. C. von Schöpf, A. Komzak, F. Braun, and E. Jacobi, Ann. Chem., 559, 1 (1948).

    Google Scholar 

  7. E. W. Petrillo and E. R. Spitzmiller, Tetrahedron Lett., No. 51, 4929 (1979).

    Google Scholar 

  8. D. Barbry, G. Ricart, and D. Couturier, Org. Magn. Reson., 17, 103 (1981).

    Google Scholar 

  9. N. S. Zefirov and N. M. Shekhtman, Usp. Khim., 40, 593 (1971).

    Google Scholar 

  10. T. A. Crabb and R. F. Newton, Tetrahedron, 24, 1997 (1968).

    Google Scholar 

  11. T. A. Crabb and P. A. Jupp, Org. Magn. Reson., 13, 63 (1980).

    Google Scholar 

  12. G. Sprague and A. Lund, in: Heterocyclic Compounds, E. Elderfield, ed., Vol. 5, Academic Press (1955).

  13. J. B. Lambert and M. W. Majchrzak, J. Am. Chem. Soc., 102, 3588 (1980).

    Google Scholar 

  14. R. Oda, M. Okano, F. Tokiura, and A. Miyafu, Bull. Chem. Soc. Jpn., 35, 1216 (1962).

    Google Scholar 

  15. F. Chanon, M. Rajzmann, M. Chanon, J. Metzger, G. Pouzard, and T., Drakenberg, Can. J. Chem., 58, 604 (1981).

    Google Scholar 

  16. F. Yu. Rachinskii, N. M. Slavachevskaya, and D. V. Ioffe, Zh. Obshch. Khim., 28, 2998 (1958).

    Google Scholar 

  17. C. C. J. Culvenor, W. Davies, and K. H. Pausacker, J. Chem. Soc., No. 11, 1050 (1946).

    Google Scholar 

  18. H. R. Snyder, J. Stewart, and J. Zeigler, J. Am. Chem. Soc., 69, 2672 (1947).

    Google Scholar 

  19. G. Tschudi and H. Schinz, Helv. Chem. Acta, 33, 1865 (1950).

    Google Scholar 

  20. H. Zondler and W. Pfleiderer, Ann., 759, 84 (1972).

    Google Scholar 

  21. A. D. Campbell, C. L. Carter, and S. W. Slater, J. Chem. Soc., No. 11, 1741 (1948).

    Google Scholar 

  22. M. Larchevêque, A. Debal, and T. Cuvigny, Bull. Soc. Chim. Fr., Nos. 7–8, 1710 (1974).

    Google Scholar 

  23. F. Salmon-Legagneur and H. des Abbayes, Compt. Rend., C, 265, 1288 (1967).

    Google Scholar 

  24. R. Bonnett, V. M. Clark, A. Giddey, and A. Todd, J. Chem. Soc., No. 6, 2087 (1959).

    Google Scholar 

  25. A. Pictet and F. W. Kay, Chem. Ber., 42, 1963 (1909).

    Google Scholar 

  26. Amer. Home Prod. Corp., British Patent No1 702985; Chem. Abstr., 49, 5515 (1955).

    Google Scholar 

  27. A. N. Kost and G. A. Golubeva, Zh. Obshch. Khim., 33, 248 (1963).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 776–785, June, 1983.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Potekhin, A.A., Sokolov, V.V., Ogloblin, K.A. et al. Addition of thiiranes to δ1-piperideines and δ1-pyrrolines. Chem Heterocycl Compd 19, 622–630 (1983). https://doi.org/10.1007/BF00523073

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00523073

Keywords

Navigation