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Chemistry of Heterocyclic Compounds

, Volume 47, Issue 12, pp 1509–1515 | Cite as

Alkylation of N-arylcyanamides and electron-deficient phenols with (chloromethyl)thiirane

  • A. N. Butkevich
  • M. Zibinsky
  • V. V. SokolovEmail author
  • A. A. Tomashevskii
Article

Alkylation of N-arylcyanamides with (chloromethyl)thiirane in aqueous alkaline solution provides an easy synthetic approach to N-aryl-N-(thietan-3-yl)cyanamides. Yields vary from 34 to 76% and are lower in the case of electron-deficient aryl substituents. The reaction with phenols containing electron-withdrawing groups results in formation of 3-(aryloxy)thietanes in 19–45% yields.

Keywords

3-aminothietanes N-arylcyanamides (chloromethyl)thiirane phenols thiirane-thietane rearrangement 

References

  1. 1.
    A. Li, Drug Discovery Today, 9, 685 (2004).CrossRefGoogle Scholar
  2. 2.
    J. Chamberlain, in: The Analysis of Drugs in Biological Fluids, CRC Press Inc., (1995), p. 67.Google Scholar
  3. 3.
    M. Sander, Chem. Rev., 66, 341 (1966).CrossRefGoogle Scholar
  4. 4.
    A. A. Tomashevskii, V. V. Sokolov, and A. A. Potekhin, Russ. J. Org. Chem., 39, 226 (2003).CrossRefGoogle Scholar
  5. 5.
    F. A. Khaliullin, V. A. Kataev, and Yu. V. Strokin, Khim. Geterotsikl. Soedin., 516 (1991). [Chem. Heterocycl. Comp., 27, 410 (1991)].Google Scholar
  6. 6.
    V. A. Kataev, L. V. Spirikhin, A. N. Khaliullin, and I. A. Gailyunas, Russ. J. Org. Chem., 38, 1507 (2002).CrossRefGoogle Scholar
  7. 7.
    E. E. Klen, F. A. Khaliullin, and G. F. Iskhakova, Russ. J. Org. Chem., 41, 1847 (2005).CrossRefGoogle Scholar
  8. 8.
    V. V. Sokolov, A. N. Butkevich, V. N. Yuskovets, A. A. Tomashevskii, and A. A. Potekhin, Russ. J. Org. Chem., 41, 1023 (2005).CrossRefGoogle Scholar
  9. 9.
    A. N. Butkevich, V. V. Sokolov, A. A. Tomashevskii, and A. A. Potekhin, Russ. J. Org. Chem., 42, 1244 (2006).CrossRefGoogle Scholar
  10. 10.
    B. Devan and K. Rajagopalan, Synth. Commun., 24, 1691 (1994).CrossRefGoogle Scholar
  11. 11.
    V. Kumar, M. P. Kaushik, and A. Mazumdar, Eur. J. Org. Chem., 11, 1910 (2008).CrossRefGoogle Scholar
  12. 12.
    F. Kurzer, Org. Synth., 31, 19 (1951).Google Scholar
  13. 13.
    K. Krowicki and J. W. Lown, J. Org. Chem., 52, 3493 (1987).CrossRefGoogle Scholar
  14. 14.
    H. King and I. M. Tonkin, J. Chem. Soc., 1063 (1946).Google Scholar
  15. 15.
    A. Gomtsyan, E. K. Bayburt, R. G. Schmidt, C. S. Surowy, P. Honore, K. C. Marsh, S. M. Hannick, H. A. McDonald, J. M. Wetter, J. P. Sullivan, M. F. Jarvis, C. R. Faltynek, and C.-H. Lee, J. Med. Chem., 51, 392 (2008).CrossRefGoogle Scholar
  16. 16.
    A. Renodon-Corniere, S. Dijols, C. Perollier, D. Lefevre-Groboillot, J.-L. Boucher, R. Attias, M.-A. Sari, D. Stuehr, and D. Mansuy, J. Med. Chem., 45, 944 (2002).CrossRefGoogle Scholar
  17. 17.
    T. Cai, M. Xian, and P. G. Wang, Bioorg. Med. Chem. Lett., 12, 1507 (2002).CrossRefGoogle Scholar
  18. 18.
    J. Anatol and J. Berecoechea, Synthesis, 111 (1975).Google Scholar
  19. 19.
    O. Foussard-Blanpin, G. Uchida-Ernouf, J. Anatol, and J. Berecoechea, Eur. J. Med. Chem., 14, 215 (1979).Google Scholar
  20. 20.
    F. F. Wong, C.-Y. Chen, and M.-Y. Yeh, Synlett, 559 (2006).Google Scholar
  21. 21.
    P. N. Gaponik, V. P. Karavai, and Y. V. Grigor'ev, Khim. Geterotsikl. Soedin., 1521 (1985). [Chem. Heterocycl. Comp., 21, 1255 (1985)]Google Scholar
  22. 22.
    P. N. Gaponik, V. P. Karavai, I. E. Davshko, M. M. Degtyarik, and A. N. Bogatikov, Khim. Geterotsikl. Soedin., 1528 (1990). [Chem. Heterocycl. Comp., 26, 1274 (1990)].Google Scholar
  23. 23.
    S. V. Voitekhovich, A. N. Vorob’ev, P. N. Gaponik, and O. A. Ivashkevich, Khim. Geterotsikl. Soedin., 1174 (2005). [Chem. Heterocycl. Comp., 41, 999 (2005)].Google Scholar
  24. 24.
    G. H. Buchanan and G. Barsky, J. Am. Chem. Soc., 52, 195 (1930).CrossRefGoogle Scholar
  25. 25.
    M. L. Naklicki and R. Crutchley, Inorg. Chem., 28, 4226 (1989).CrossRefGoogle Scholar
  26. 26.
    S. S. Ahmad, S. I. Haider, and I. Fatima, Synth. Commun., 17, 1861 (1987).CrossRefGoogle Scholar
  27. 27.
    L.-Y. Hu, J. Guo, S. S. Magar, J. B. Fischer, K. J. Burke-Howie, and G. J. Durant, J. Med. Chem., 40, 4281 (1997).CrossRefGoogle Scholar
  28. 28.
    F. Arndt and B. Rosenau, Ber. Dtsch. Chem. Ges., 50, 1248 (1917).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • A. N. Butkevich
    • 1
  • M. Zibinsky
    • 2
  • V. V. Sokolov
    • 3
    Email author
  • A. A. Tomashevskii
    • 3
  1. 1.University of Southern CaliforniaLos AngelesUSA
  2. 2.The Scripps Research InstituteLa JollaUSA
  3. 3.Saint Petersburg State UniversitySt. PetersburgRussia

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