Abstract
A new method was developed for the electrophilic introduction of methylthio group into a series of aromatic heterocyclic compounds through the hetaryl(dimethyl)sulfonium salts formed in the course of the reaction of the respective heterocycles with the complex of dimethyl sulfide and trifluoromethanesulfonic anhydride. By demethylation with triethylamine it was possible to obtain the methylthio-substituted heterocycles.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
P. J. Stang, M. Hanack, and L. R. Subramanian,Synthesis, 85 (1982).
G. Maas and P. J. Stang,J. Org. Chem.,46, 1606 (1981).
X. Creary,J. Org. Chem.,45, 2727 (1980).
V. G. Nenajdenko, P. V. Vertelezkij, A. B. Koldobskij, I. V. Alabugin, and E. S. Balenkova,J. Org. Chem.,62, 2483 (1997).
P. Claus and W. Rieder,Tetrahedron Lett., No. 37, 3879 (1972).
M. J. Hatch, M. Yoshimine, D. L. Schmidt, and H. B. Smith,J. Am. Chem. Soc.,93, 4671 (1971).
G. H. Wiegand and W. E. McEwen,J. Org. Chem.,33, 2671 (1968).
Houben-Weyl,Methoden der Organischen Chemie, Thieme Verlag Stuttgart,E11, 469 (1985).
Ya. L. Gol'dfarb, N. S. Ksenzhek, and L. I. Belen'kii,Khim. Geterotsikl. Soedin., No. 2, 165 (1972).
V. G. Nenajdenko and E. S. Balenkova,Tetrahdron,50, 12407 (1994).
V. G. Nenajdenko, P. V. Vertelezkij, and E. S. Balenkova,Sulfur Lett.,20, 75 (1996).
E. J. Corey and M. Chaykovsky,J. Am. Chem. Soc.,84, 867 (1962).
K. H. Park and G. D. Daves,J. Org. Chem.,45, 780 (1980).
H. H. Wendebourg and K., Hartke.Synthesis, 329 (1989).
M. V. Lebedev, V. G. Nenajdenko, and E. S. Balenkova,Tetrahedron,54, 5599 (1998).
K. H. Park, G. A. Gray, and G. D. Daves,J. Am. Chem. Soc.,100, 7475 (1978).
Ya. L. Gol'dfarb, M. A. Kalik, and M. L. Kirmalova,Zh. Obshch. Khim.,29, 2034 (1959).
F. J. Schuetz,J. Org. Chem.,27, 1301 (1962).
B. Capon and S. O. Lew,Tetrahedron,48, 7823 (1992).
R. M. Acheson, M. J. Ferris, S. R. Critchley, and D. J. Watkin,J. Chem. Soc. Perkin Trans. 2, 326 (1980).
N. I. Baranova and V. I. Shishkina,Khim. Geterotsikl. Soedin., No. 8, 1076 (1971).
P. G. Gassmen,J. Am. Chem. Soc.,96, 5495 (1974).
Additional information
M. V. Lomonosov Moscow State University. Moscow; e-mail: nen@acylium.chem.msu.ru. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 171–177, February, 2000.
Rights and permissions
About this article
Cite this article
Shevchenko, N.E., Karpov, A.S., Zakurdaev, E.P. et al. Synthesis of methylthiosubstituted heterocycles using the complex of trifluoromethanesulfonic anhydride with dimethyl sulfide. Chem Heterocycl Compd 36, 137–143 (2000). https://doi.org/10.1007/BF02283541
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02283541