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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 2, pp 189–192 | Cite as

Synthesis of 4-polyfluoroalkyl-1,3-dithiolanes via [3+2] cycloaddition of thiocarbonyl ylide to polyfluoroalkanethioamides

  • Sergiy S. MykhaylychenkoEmail author
  • Yuriy N. Markitanov
  • Timofii V. Rudenko
  • Eduard B. Rusanov
  • Yuriy G. Shermolovich
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New 4-polyfluoroalkyl-1,3-dithiolanes were synthesized by reaction of polyfluoroalkanethioamides with thiocarbonyl ylide that was generated in situ by desilylation of chloromethyl (trimethylsilyl)methyl sulfide with tetramethylammonium fluoride.

Keywords

1,3-dithiolane polyfluoroalkanethiocarboxylic acids thioamide thiocarbonyl ylide [3+2] cycloaddition 

References

  1. 1.
    (a) Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications; Petrov, V. A., Ed.; John Wiley & Sons, Inc.: Hoboken, New Jersey, 2009. (b) Gakh, A. A.; Shermolovich, Yu. G. Curr. Top. Med. Chem. 2014, 14, 952.Google Scholar
  2. 2.
    (a) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305. (b) Hagmann, W. K. J. Med. Chem. 2008, 51, 4359. (c) Prakash, G. K. S.; Chacko, S. Curr. Opin. Drug Discovery Dev. 2008, 11, 793.Google Scholar
  3. 3.
    (a) Shermolovich, Yu. G.; Pazenok, S. V. Top. Heterocycl. Chem. 2012, 27, 101. (b) Fluorine in Heterocyclic Chemistry; Nenajdenko, V. G., Ed.; Springer: Heidelberg, 2014.Google Scholar
  4. 4.
    Davis, F. A.; Kasu, P. V. N. Org. Prep. Proc. Int. 1999, 31, 125.CrossRefGoogle Scholar
  5. 5.
    (а) Timoshenko, V. M.; Siry, S. A.; Rozhenko, A. B.; Shermolovich, Yu. G. J. Fluorine Chem. 2010, 131, 172. a Siry, S. A.; Timoshenko, V. M. Tetrahedron Lett. 2010, 51, 6406. b Mikhailichenko, S. S.; Bouillon, J.-P.; Besson, T.; Shermolovich, Yu. G. Tetrahedron Lett. 2010, 51, 990.Google Scholar
  6. 6.
    Mloston, G.; Romanski, Ya.; Rusanov, E. B.; Chernega, A. N.; Shermolovich, Yu. G. Zh. Org. Khim., 1995, 31, 1027.Google Scholar
  7. 7.
    Mykhaylychenko, S. S.; Siryi, S. A.; Pikun, N. V.; Shermolovich, Yu. G. Chem. Heterocycl. Compd. 2015, 51, 861. [Khim. Geterotsikl. Soedin. 2015, 51, 861.]Google Scholar
  8. 8.
    Mykhaylychenko, S. S.; Pikun, N. V.; Rusanov, E. B.; Rozhenko, A. B.; Shermolovich, Yu. G. Chem. Heterocycl. Compd. 2017, 53, 1268. [Khim. Geterotsikl. Soedin. 2017, 53, 1268.]CrossRefGoogle Scholar
  9. 9.
    Hosomi, A.; Matsuyama, Y.; Sakurai, H. J. Chem. Soc., Chem. Commun. 1986, 1073.Google Scholar
  10. 10.
    Middleton, W. J.; Sharkey W. H. J. Org. Chem. 1965, 30, 1384.CrossRefGoogle Scholar
  11. 11.
    Popkova, V. Ya.; Bekker, R. A.; Mysov, E. I.; Galakhov, M. V.; Knunyants, I. L. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1985, 34, 2536. [Izv. Akad. Nauk SSSR, Ser. Khim. 1985, 2740.]Google Scholar
  12. 12.
    (a) Mloston, G.; Linden, A.; Heimgartner, H. Helv. Chim. Acta 1991, 74, 1386. (b) Huisgen, R.; Li, X.; Mloston, G.; Fulka, C. Eur. J. Org. Chem. 2000, 1695.Google Scholar
  13. 13.
    Mykhaylychenko, S. S.; Bouillon, J.-P.; Shermolovich, Yu. G. J. Fluorine Chem. 2009, 130, 878.CrossRefGoogle Scholar
  14. 14.
    Karlson, S.; Högberg, H.-E. Org. Lett. 1999, 1, 1667.CrossRefGoogle Scholar
  15. 15.
    Pikun, N. V.; Mykhaylychenko, S. S.; Rusanov, E. B.; Shermolovich, Yu. G. Russ. J. Org. Chem. 2013, 49, 1572. [Zh. Org. Khim. 2013, 49, 1597.]Google Scholar
  16. 16.
    Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.Google Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Sergiy S. Mykhaylychenko
    • 1
    Email author
  • Yuriy N. Markitanov
    • 1
  • Timofii V. Rudenko
    • 2
  • Eduard B. Rusanov
    • 1
  • Yuriy G. Shermolovich
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKyivUkraine
  2. 2.Enamine Ltd.KyivUkraine

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