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Synthesis of Functionally-substituted Pyrrolothiazolidines from Pyrrole-2-carbodithioates, CH-acids, and Haloacetylenes

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Functionally substituted pyrrolothiazolidines have been synthesized by the sequential treatment of pyrrole-2-carbodithioates with methylene-reactive nitriles and haloacetylenes in a KOH-DMSO system.

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REFERENCES

  1. C. O. Wilson, O. Gisvold, and R. F. Doerge, Textbook of Medicinal and Pharmaceutical Chemistry, Pitman, London (1966).

    Google Scholar 

  2. Specialist Periodical Reports. Sulphur, Selenium, and Tellurium, The Chemical Society, London, (a) 1970, 1; (b) 1973, 2; (c) 1975, 3.

  3. P. Haacke, L. P. Bausher, and J. P. McNeal, J. Am. Chem. Soc., 93, 7045 (1971).

    Google Scholar 

  4. F. Kurtzer, see Ref. 2a, Chap. 13.

  5. F. Kurtzer, see Ref. 2c, Chap. 14.

  6. M. Fiorentino, L. Testferri, M. Tiecco, and L. Troisi, J. Chem. Soc., Chem. Commun., 317 (1977).

  7. L. N. Sobenina, A. I. Mikhaleva, M. P. Sergeeva, O. V. Petrova, T. S. Aksamentova, O. B. Kozyreva, D. S. D. Toryashinova, and B. A. Trofimov, Tetrahedron, 51, 4223 (1995).

    Google Scholar 

  8. B. A. Trofimov, 1st Florida Heterocyclic Course & Conference, Univ. of Florida, Gainesville, Florida (2000), F-1 to F-18.

    Google Scholar 

  9. L. N. Sobenina, A. I. Mikhaleva, M. P. Sergeeva, D.-S. D. Toryashinova, O. V. Kozyreva, and B. A. Trofimov, Khim. Geterotsikl. Soedin., 919 (1996).

  10. L. N. Sobenina, A. I. Mikhaleva, D. S. D. Toryashinova, and B. A. Trofimov, Sulfur Lett., 20, 9 (1996).

    Google Scholar 

  11. L. N. Sobenina, A. I. Mikhaleva, D. S. D. Toryashinova, O. B. Kozyreva, and B. A. Trofimov, Sulfur Lett., 21, 205 (1997).

    Google Scholar 

  12. L. N. Sobenina, A. P. Demenev, A. I. Mikhaleva, O. V. Petrova, L. I. Larina, G. P. Chernykh, D. S. D. Toryashinova, A. V. Vaschenko, and B. A. Trofimov, Sulfur Lett., 24, 1 (2000).

    Google Scholar 

  13. J. I. Dickstein and S. I. Miller, in: S. Patai (editor), The Chemistry of the Carbon-Carbon Triple Bond, Part 2, Wiley, New York (1978), p. 917.

    Google Scholar 

  14. S. I. Miller, C. E. Orzech, C. A. Welch, G. R. Ziegler, and J. I. Dickstein, J. Am. Chem. Soc., 84, 2020 (1962).

    Google Scholar 

  15. J. Arens, Rec. Trav. Chim., 82, 183 (1963).

    Google Scholar 

  16. S. Oae, Organic Chemistry of Sulfur, Plenum, New York (1974), 688 pp.

    Google Scholar 

  17. T. N. Komarova, A. S. Nakhmanovich, T. E. Glotova, V. N. Elokhina, A. I. Albanov, and V. A. Lopyrev, Izv. Akad. Nauk, Ser. Khim., 199 (1997).

  18. A. V. Afonin, M. V. Sigalov, S. E. Korostova, I. A. Aliev, A. V. Vashchenko, and B. A. Trofimov, Magn. Reson. Chem., 28, 580 (1990).

    Google Scholar 

  19. V. Wolf and F. Kowitz, Liebigs Ann. Chem., 638, 22 (1960).

    Google Scholar 

  20. A. N. Mirskova, S. G. Seredkina, and M. G. Voronkov, Sulfur Rep., 9, No. 2, 75 (1989).

    Google Scholar 

  21. S. G. D'yachkova, N. K. Gusarova, E. A. Nikitina, L. I. Larina, L. M. Sigalov, A. V. Abramov, and B. A. Trofimov, Zh. Obshch. Khim., in the press.

  22. A. V. Afonin, I. A. Ushakov, S. V. Zinchenko, O. A. Tarasova, and B. A. Trofimov, Magn. Reson. Chem., 38, 994 (2000).

    Google Scholar 

  23. J. Jeener, B. H. Meier, and R. R. Ernst, J. Chem. Phys., 69, 4546 (1979).

    Google Scholar 

  24. A. Kumar, K. Nagayama, and R. R. Ernst, J. Magn. Reson., 40, 321 (1980).

    Google Scholar 

  25. A. Bax, and S. Subramanian, J. Magn. Reson., 67, 565 (1986).

    Google Scholar 

  26. A. Bax and S. Summers, J. Am. Chem. Soc., 108, 2093 (1986).

    Google Scholar 

  27. B. A. Trofimov, L. N. Sobenina, A. I. Mikhaleva, M. P. Sergeeva, and R. I. Polovnikova, Sulfur Lett., 15, 219 (1992).

    Google Scholar 

  28. J. Reisch and H. Welker, Arch. Pharm., 297, 628 (1964).

    Google Scholar 

  29. A. N. Mirskova, S. G. Seredkina, and M. G. Voronkov, USSR Inventor's Certificate 1204616; Chem. Abstr., 105, 20846 (1987).

    Google Scholar 

  30. F. Straus, L. Kollek, and W. Heyn, Chem. Ber., 63, 1868 (1930).

    Google Scholar 

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Sobenina, L.N., Demenev, A.P., Mikhaleva, A.I. et al. Synthesis of Functionally-substituted Pyrrolothiazolidines from Pyrrole-2-carbodithioates, CH-acids, and Haloacetylenes. Chemistry of Heterocyclic Compounds 38, 86–94 (2002). https://doi.org/10.1023/A:1014863511588

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