Selective methods were developed for the synthesis of N-aryl-1,5,3-dithiazepinanes and N-aryl-1,5,3-dithiazocinanes by transamination of N-tert-butyl-1,5,3-dithiazepinane or recyclization of 1-oxa-3,6-dithiacycloheptane and 1-oxa-3,7-dithiacyclooctane by the action of aniline derivatives in the presence of Sm(NO3)3·6H2O catalyst.
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References
T. W. Jackson, M. Kojima, R. M. Lambrecht, N. Marubayashi, and M. Hiratake, Aust. J. Chem., 47, 2271 (1994).
M. Sako, Y. Kojima, K. Hirota, and Y. Maki, Heterocycles, 22, 1017 (1984).
V. R. Akhmetova, G. R. Khabibullina, E. B. Rakhimova, R. A. Vagapov, R. R. Khairullina, Z. T. Niatshina, and N. N. Murzakova, Mol. Diversity, 14, 463 (2010).
K. S. Shmuilovich, N. A. Orlova, I. V. Beregovaya, and V. V. Shelkovnikov, Izv. Akad. Nauk, Ser. Khim., 354 (2011).
G. L. Khatik, R. Kumar, and A. K. Chakraborti, Synthesis, 541 (2007).
A. Tsotinis, A. Eleutheriades, L. Di Bari, and G. J. Pescitelli, J. Org. Chem., 72, 8928 (2007).
M. V. Vovk, V. I. Dorokhov, V. I. Boiko, and L. I. Samarai, Khim. Geterotsikl. Soedin., 1472 (1993). [Chem. Heterocycl. Compd., 29, 1265 (1993).]
P. D. Bailey, A. N. Boa, and J. Clayson, Tetrahedron, 65, 1724 (2009).
A. V. Vovk and L. M. Zaitsev, Khim.-farm. Zh., 27, No. 12, 26 (1993).
R. V. Kunakova, S. R. Khafizova, Yu. S. Dal'nova, R. S. Aleev, L. M. Khalilov, and U. M. Dzhemilev, Neftekhimiya, 42, 382 (2002).
N. Nohyaku, JP Pat. Appl. 60004177; Chem. Abstr., 102, 149292d (1985).
U. M. Dzhemilev, R. S. Aleev, Yu. S. Dal'nova, R. V. Kunakova, and S. R. Khafizova, RF Pat. 2206726; Byul. Izobret., No. 17, 730 (2003).
S. Yadav Lal Dhar, A. Vaish, and S. Sharma, J. Agric. Food Chem., 42, 811 (1994).
P. Farkas, J. Sadecka, M. Kovac, B. Siegmund, E. Leitner, and W. Pfannhauser, Food Chem., 60, 617 (1997).
K. Ito and M. Sekiya, Chem. Pharm. Bull., 27, 1691 (1979).
U. Wellmar, J. Heterocycl. Chem., 35, 1531 (1998).
Z. T. Niatshina, N. N. Murzakova, I. V. Vasilieva, E. B. Rakhimova, V. R. Akhmetova, and A. G. Ibragimov, ARKIVOC, viii, 141 (2011).
N. V. Russavskaya, V. A. Grabel'nikh, E. P. Levanova, E. N. Sukhomazova, and E. N. Deryagina, Zh. Org. Khim., 38, 1551 (2002).
N. N. Murzakova, E. B. Rakhimova, I. V. Vasilieva, K. I. Prokof'yev, A. G. Ibragimov, and U. M. Dzhemilev, Tetrahedron Lett., 52, 4090 (2011).
V.G. Kharchenko, T. I. Gubina, and I. A. Markushina, Zh. Org. Khim., 18, 394 (1982).
S. P. Voronin, T. I. Gubina, S. A. Trushin, I. A. Markushina, and V. G. Kharchenko, Khim. Geterotsikl. Soedin., 1458 (1989). [Chem. Heterocycl. Compd., 25, 1216 (1989).]
G. V. Mokrov, A. M. Likhosherstov, V. P. Lezina, T. A. Gudasheva, I. S. Bushmarinov, and M. Yu. Antipin, Izv. Akad. Nauk, Ser. Khim., 1228 (2010).
K. Krohn and S. Cludius-Brandt, Synthesis, 1344 (2010).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1132-1139, July, 2012.
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Rakhimova, E.B., Vasil’yeva, I.V., Khalilov, L.M. et al. Effective synthesis of N-aryl-substituted 1,5,3-dithiazepinanes and 1,5,3-dithiazocinanes. Chem Heterocycl Comp 48, 1050–1057 (2012). https://doi.org/10.1007/s10593-012-1098-8
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DOI: https://doi.org/10.1007/s10593-012-1098-8