Sulfenylating reagents have been obtained by the action of sulfuryl chloride or antimony pentachloride on di(2-pyridyl) disulfide. Their interaction with alkenes proceeds as addition-cyclization with ring closure by the nitrogen atom of the pyridine fragment of the sulfur-containing electrophile with the formation of 2,3-dihydro[1,3]thiazolo[3,2-a]pyridinium derivatives.
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A. V. Borisov, V. K. Belsky, V. K. Osmanov, G. N. Borisova, and Zh. V. Matsulevich, Khim. Geterotsikl. Soedin., 1558 (2006). [Chem. Heterocycl. Compd., 42, 1346 (2006).]
A. V. Borisov, V. K. Belsky, G. N. Borisova, V. K. Osmanov, Zh. V. Matsulevich, and T. V. Goncharova, Khim. Geterotsikl. Soedin., 763 (2001). [Chem. Heterocycl. Compd., 37, 702 (2001)].
A. V. Borisov, V. K. Belsky, T. V. Goncharova, G. N. Borisova, V. K. Osmanov, Zh. V. Matsulevich, N. G. Frolova, and E. D. Savin, Khim. Geterotsikl. Soedin., 893 (2005). [Chem. Heterocycl. Comp., 41, 771 (3005)].
A. V. Borisov, Zh. V. Matsulevich, V. K. Osmanov, G. N. Borisova, and E. V. Savikhina, Khim. Geterotsikl. Soedin., 628 (2007). [Chem. Heterocycl. Compd., 43, 525 (2007)].
A. V. Borisov and Zh. V. Matsulevich, Khim. Geterotsikl. Soedin., 1103 (2009). [Chem. Heterocycl. Comdp., 45, 884 (2009)].
A. V. Borisov, V. K. Osmanov, G. N. Borisova, Z. V. Matsulevich, and G. K. Fukin, Mendeleev Commun., 19, 49 (2009).
J. V. Castell and A. Tun-Kyi, Helv. Khim. Acta, 62, 2507 (1979).
V. V. Samukov, Synth. Commun., 28, 3213 (1998).
A. V. Borisov, Zh. V. Matsulevich, V. K. Osmanov, G. N. Borisova, G. Z. Mammadova, A. M. Maharramov, and V. N. Khrustalev, Khim. Geterotsikl. Soedin., 1034 (2012). [Chem. Heterocycl. Compd., 48, 963 (2012)].
A. V. Borisov, Zh. V. Matsulevich, V. K. Osmanov, G. N. Borisova, G. Z. Mammadova, A. M. Maharramov, and V. N. Khrustalev, Khim. Geterotsikl. Soedin., 1167 (2012). [Chem. Heterocycl. Compd., 48, 1085 (2012)].
A. Ohta and Y. Yamashita, Mol. Cryst. Liq. Cryst. Sci. Technol. Sect. A, 296, 1 (1997).
H. L. Byers, K. B. Dillon, and A. E. Goeta, Inorg. Chim. Acta, 344, 239 (2003).
S. Chaabouni, J. M. Savariault, and A. B. Salah, J. Chem. Crystallogr., 34, 661 (2004).
A. Angeloni, P. C. Crawford, A. G. Orpen, T. J. Podesta, and B. J. Shore, Chem.-Eur. J., 10, 3783 (2004).
A. Earnshaw and N. Greenwood, Chemistry of the Elements, 2nd ed., Butterworth-Heinemann, Oxford (1997), p. 567.
P. Kovacic and A. K. Sparks, J. Am. Chem. Soc., 82, 5740 (1960).
J. Bertin, J. L. Luche, H. B. Kagan, and R. Setton, Tetrahedron Lett., 9, 763 (1974).
S. Uemura, A. Onoe, and M. Okano, Bull. Chem. Soc. Jpn., 47, 692 (1974).
S. Uemura, A. Onoe, and M. Okano, J. Chem. Soc., Chem. Commun., 145 (1976).
V. L. Heasley, K. D. Rold, D. R. Titterington, C. T. Leach, B. T. Gipe, D. B. McKee, and G. E. Heasley, J. Org. Chem., 41, 3997 (1976).
W. A. Nugent, J. Org. Chem., 45, 4533 (1980).
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*For Communication 3, see [1].
Translated from Chemistry of Heterocyclic Compounds, No. 7, pp. 1180-1186, July, 2012.
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Borisov, A.V., Matsulevich, Z.V., Osmanov, V.K. et al. Sulfenyl halides in the synthesis of heterocycles. 4*. Heterocyclization in reactions of alkenes with sulfenylating reagents based on di(2-pyridyl) disulfide. Chem Heterocycl Comp 48, 1098–1104 (2012). https://doi.org/10.1007/s10593-012-1104-1
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DOI: https://doi.org/10.1007/s10593-012-1104-1