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Abstract
The reaction of 1,1-bis(methylthio)-2-nitroethylene with various aromatic amines produces 1-methylthio-2-nitrovinyl arylamines derivatives in excellent yields. The reactions occur in ethanol as solvent and avoiding the addition of any catalyst. The workup procedure is very simple and the products do not require further purification.
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References
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References
D.H.R. Barton, D. Crich and G. Kretzschmar, Tetrahedron Lett., 25, 1055 (1984); http://dx.doi.org/10.1016/S0040-4039(01)80099-X.
N.I. Drake and C.M. Kraebel, J. Org. Chem., 26, 41 (1961); http://dx.doi.org/10.1021/jo01060a008.
K.R. Loos and H.H. Gunthard, J. Chem. Phys., 46, 1200 (1967); http://dx.doi.org/10.1063/1.1840793.
C. Bhanja and J. Satyaban, Int. J. Pharm. Technol., 4, 4850 (2013).
S.P Maybhate, A.R.A.S Deshmukh and S Rajappa, Tetrahedron Lett., 47, 3887 (1990); http://dx.doi.org/10.1016/S0040-4020(01)80911-X.
(a) J.A. Zablocki, M. Miyano, R.B. Garland, D. Pireh, L. Schretzman, S.N. Rao, R.J. Lindmark, S.G. Panzer-Knodle and N.S. Nicholson, J. Med. Chem., 36, 1811 (1993); http://dx.doi.org/10.1021/jm00065a003.;
(b) L. Peterlin-Masic and D. Kikelj, Tetrahedron, 57, 7073 (2001); http://dx.doi.org/10.1016/S0040-4020(01)00507-5.
H. Nishiwaki, Y. Nakagawa, T. Ueno, S. Kagabu and K. Nishimura, Pest Manag. Sci., 57, 810 (2001); http://dx.doi.org/10.1002/ps.362.
H. Nishiwaki, H. Nagaoka, M. Kuriyama, S. Yamauchi and Y. Shuto, Biosci. Biotechnol. Biochem., 75, 780 (2011); http://dx.doi.org/10.1271/bbb.100846.
J.A. Tucker, T.L. Clayton, C.G. Chidester, M.W. Schulz, L.E. Harrington, S.J. Conrad, Y. Yagi, N.L. Oien, D. Yurek and M.-S. Kuo, Bioorg. Med. Chem., 8, 601 (2000); http://dx.doi.org/10.1016/S0968-0896(99)00319-3.
C.A. Buschi and A.B. Pomiluo, Phytochemistry, 26, 863 (1987); http://dx.doi.org/10.1016/S0031-9422(00)84810-4.
R. de la Rosa, V. Martínez-Barrasa, C. Burgos and J. Alvarez-Builla, Tetrahedron Lett., 41, 5837 (2000); http://dx.doi.org/10.1016/S0040-4039(00)00839-X.
G.V. Boyd, in eds.: S. Patai and Z. Rappoport, The Chemistry of Amidines and lmidates, vol. 2, John Wiley, New York, pp. 367-424 (1991).
F. Richter and H.H. Otto, Tetrahedron Lett., 28, 2945 (1987); http://dx.doi.org/10.1016/S0040-4039(00)96250-6.
R.D. Little and M.R. Masjedizadeh, The Intramolecular Michael Reaction in Organic Reactions, John Wiley, New York (1995).
M. Naka, T. Nanbu, K. Kobayashi, Y. Kamanaka, M. Komeno, R. Yanase, T. Fukutomi, S. Fujimura, H.G. Seo, N. Fujiwara, S. Ohuchida, K. Suzuki, K. Kondo and N. Taniguchi, Biochem. Biophys. Res. Commun., 270, 663 (2000); http://dx.doi.org/10.1006/bbrc.2000.2474.
H. He, M. Liu, Z. Zheng, Y. Liu, J. Xiao, R. Su, C. Hu, J. Li and S. Li, Molecules, 11, 393 (2006); http://dx.doi.org/10.3390/11060393.
S. Yaya, B. Fante, S. Sorho, C. Jean-Marie and A.A. Augustin, J. Chem. Sci., 119, 259 (2007); http://dx.doi.org/10.1007/s12039-007-0034-4.
Y. Soro, F. Bamba, S. Siaka and J.-M. Coustard, Tetrahedron Lett., 47, 3315 (2006); http://dx.doi.org/10.1016/j.tetlet.2006.03.003.
V.V. Perekalin and E.S. Lipina, Conjugated Nitro Compounds, Wiley, Chichester (1994).