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Synthesis and Reactions of Benzimidazoline-2-thione Derivatives

  • Lee Tae Ryong (Department of Chemistry, Seoul National University) ;
  • Kim Kyongtae (Department of Chemistry, Seoul National University)
  • Published : 19890200

Abstract

Two properties of sodium naphthalenide (2), i.e. a strong base and a good electron donor were utilized for one pot synthesis: 2-alkylthiobenzimidazoles were synthesized in excellent yields from the reactions of benzimidazoline-2-thione (1) with an equimolar amount of alkyl halides in the presence of 2. Continuous addition of a different alkyl halide without the isolation of 2-alkylthiobenzimidazoles afforded 1-alkyl-2-alkylthiobenzimidazoles having different alkyl groups at N and S atoms in excellent yields. Further addition of 2 to 1-alkyl-2-alkylthiobenzimidazoles gave excellent yields of 1-alkylbenzimidazoline-2-thiones. When 2 in THF was added to a suspension of 1-alkyl-2-alkylthiobenzimidazoles in THF, a bond cleavage between N and C of alkyl group as well as S and C of alkyl group occurred. This is in contrast to the observation in which only cleavage between S and C of alkyl group takes place in the homogeneous solution.

Keywords

References

  1. Tetrahedron Letts. J. A. Vida
  2. U.S. Patent 3,927,014 C. Rovnyah;V. L. Narayanan;R. D. Haugwitz;C. M. Cimarusti
  3. Chem. Abstr. v.84 C. Rovnyah;V. L. Narayanan;R. D. Haugwitz;C. M. Cimarusti
  4. J. Chem. Soc. Perkin II R. J. Badger;G. B. Barlin
  5. J. Chem. Soc. E. Hoggarth
  6. J. Heterocyclic Chem. v.20 O. P. Suri;R. K. Khajuria;D. B. Saxena;N. S. Rawat;C. K. Atal
  7. Aust. J. Chem. v.34 B. Stanovnik;M. Tisler;A. Hribar;G. B. Barlin;D. J. Brown
  8. Izv. Vyssh. Uchebn. Zaved. Khim. Khim. Tekhnol. v.19 E. V. Logachev;M. V. Povstanyanoi;P. M. Kochergin;Yu. I. Beilis
  9. Chem. Abstr. v.85 E. V. Logachev;M. V. Povstanyanoi;P. M. Kochergin;Yu. I. Beilis
  10. Nauch. Doklady Vysshei, Shkoly, Khim. Khim. Tekhnol no.2 N. P. Bednyagina;I. Ya. Postovskii
  11. Chem. Abstr. v.54 N. P. Bednyagina;I. Ya. Postovskii
  12. Uzb. Khim. Zh. v.17 K. V. Ananeva;N. K. Rozhkova
  13. Chem. Abstr. v.62 K. V. Ananeva;N. K. Rozhkova
  14. J. Heterocyclic Chem.
  15. Chem. Rev. v.74 no.2 N. L. Holy
  16. Accounts Chem. Res. v.11 J. F. Bunnett
  17. J. Am. Chem. Soc. v.93 S. Bank;B. Bockrath
  18. Accounts Chem. Res. v.4 J. F. Garst
  19. J. Pharm. Soc. Jap. v.74 K. Futaki
  20. Zhur. Priklad. Khim. v.34 G. N. Tyurenkova;E. I. Silina;I. Ya. Postovskii
  21. Chem. Abstr. v.56 G. N. Tyurenkova;E. I. Silina;I. Ya. Postovskii
  22. Bull. Inst. Chem. Res. v.43 no.3 S. Kunichika;S. Oka;T. Sugiyama
  23. Chem. Abstr. v.64 S. Kunichika;S. Oka;T. Sugiyama

Cited by

  1. ChemInform Abstract: Synthesis and Reactions of Benzimidazoline‐2‐thione Derivatives. vol.20, pp.31, 1989, https://doi.org/10.1002/chin.198931142