Abstract
An efficient one-pot procedure has been developed for the synthesis of bis-1,5,3-dithiazepanes by reaction of ethane-1,2-dithiol with formaldehyde and ammonium salts. According to the X-ray diffraction data, the heterorings in 3,3′-[ethane-1,2-diylbis(sulfanediylmethanediyl)]bis(1,5,3-dithiazepane) in crystal adopt a chair conformation with axial orientation of the substituent on the nitrogen atom.
Similar content being viewed by others
References
Pozharskii, A.F., Soldatenkov, A., and Katritzky, A.R., Heterocycles in Life and Society: An Introduction to Heterocyclic Chemistry, Biochemistry and Applications, New York: Wiley, 2011, 2nd ed.
Akhmetova, V.R., Nadyrgulova, G.R., Niatshina, Z.T., and Dzhemilev, U.M., Khim. Geterotsikl. Soedin., 2009, p. 1443.
Akhmetova, V.R., Khabibullina, G.R., Rakhimova, E.B., Vagapov, R.A., Khairullina, R.R., Niatshina, Z.T., and Murzakova, N.N., Mol. Diversity, 2010, vol. 14, p. 463.
Akhmetova, V.R., Nadyrgulova, G.R., Tyumkina, T.V., Starikova, Z.A., Golovanov, D.G., Antipin, M.Yu., Kunakova, R.V., and Dzhemilev, U.M., Izv. Akad. Nauk, Ser. Khim., 2006, p. 1758.
Akhmetova, V.R., Vagapov, R.A., Nadyrgulova, G.R., Tyumkina, T.V., Starikova, Z.A., Antipin, M.Y., Kunakova, R.V., and Dzhemilev, U.M., Tetrahedron, 2007, vol. 63, p. 11 702.
Akhmetova, V.R., Khairullina, R.R., Nadyrgulova, G.R., Kunakova, R.V., and Dzhemilev, U.M., Russ. J. Org. Chem., 2008, vol. 44, p. 190.
Akhmetova, V.R., Niatshina, Z.T., Khabibullina, G.R., Bushmarinov, I.S., Borisova, A.O., Starikova, Z.A., Korzhova, L.F., and Kunakova, R.V., Izv. Akad. Nauk, Ser. Khim., 2010, p. 980.
Dronov, V.I., Nigmatullina, R.F., Khalilov, L.M., and Nikitin, Yu E., Zh. Org. Khim., 1979, vol. 15, p. 1709.
Ito, K. and Sekiya, M., Chem. Pharm. Bull., 1979, vol. 27, p. 1691.
Murzakova, N.N., Prokof’ev, K.I., Tyumkina, T.V., and Ibragimov, A.G., Russ. J. Org. Chem., 2012, vol. 48, p. 588.
Rakhimova, E.B., Efremova, E.A., Bushmarinov, I.S., Goloveshkin, A.S., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Tetrahedron Lett., 2012, vol. 53, p. 4225.
Rakhimova, E.B., Vasil’eva, I.V., Khalilov, L.M., Ibragimov, A.G., and Dzhemilev, U.M., Khim. Geterotsikl. Soedin., 2012, vol. 7, p. 1132.
Akhmetova, V.R., Nadyrgulova, G.R., Tyumkina, T.V., Starikova, Z.A., Antipin, M.Yu., Kunakova, R.V., and Dzhemilev, U.M., Russ. J. Org. Chem., 2007, vol. 43, p. 918.
Alder, R.W., Heilbronner, E., Honnegger, E., McEwen, A.B., Moss, R.E., Olefirowicz, E., Pethyllo, P.A., Sessions, R.B., Weisman, G.R., White, J.M., and Yang, Z.-Z., J. Am. Chem. Soc., 1993, vol. 115, p. 6580.
Sheldrick, G.M., SHELXTL. Version 5. Software Reference Manual, Madison, WI: Siemens Industrial Automation, 1994.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © G.R. Khabibullina, V.R. Akhmetova, I.S. Bushmarinov, A.G. Ibragimov, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 10, pp. 1563–1567.
Rights and permissions
About this article
Cite this article
Khabibullina, G.R., Akhmetova, V.R., Bushmarinov, I.S. et al. One-pot synthesis of bis-1,5,3-dithiazepanes from ethane-1,2-dithiol, formaldehyde, and ammonium salts. Russ J Org Chem 49, 1542–1545 (2013). https://doi.org/10.1134/S1070428013100229
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428013100229