Abstract
An efficient method for the synthesis of 6-thienyl-substituted 2-amino-3-cyanopyridines by the ring transformation in the corresponding pyrimidines was developed. Further modification of the pyridines obtained under conditions of a room temperature aerobic Suzuki reaction in the presence of trans-bis(dicyclohexylamine)palladium(II) acetate as a catalyst was studied
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M. W. Beukers, I. Meurs, A. P. Ijzerman, Med. Res. Rev., 2006, 26, 667.
US Pat. 6030969; Chem. Abstrs, 2000, 132, 180592.
M. Mantri, O. de Graaf, J. van Veldhoven, A. Göblyös, J. K. von Frijtag Drabbe Künzel, T. Mulder-Krieger, R. Link, H. de Vries, M. W. Beukers, J. Brussee, A. P. Ijzerman, J. Med. Chem., 2008, 51, 4449.
WO 2004055015; Chem. Abstrs, 2004, 141, 89018n.
WO 2004054505; Chem. Abstrs, 2004, 141, 89013g.
DE Pat. 4117802; Chem. Abstrs, 1992, 118, 191550s.
K. M. Ghoneim, M. M. Badran, M. A. Shaaban, S. El-Meligie, Egypt. J. Pharm. Sci., 1988, 29, 553.
M. M. Ghorab, A. Y. Hassan, Phosphorus, Sulfur, Silicon Relat. Elem., 1998, 141, 251.
P. Verma, N. Kumar, S. Bhargava, A. K. Yadav, Indian J. Heterocycl. Chem., 2007, 16, 387.
D. C. Mungra, M. P. Patel, R. G. Patel, ARKIVOC, 2009, XIV, 64.
DD Pat. 287260; Chem. Abstrs, 1991, 114, 207041g.
R. Troschutz, T. Dennstedt, Arch. Pharm. (Weinheim), 1994, 327, 33.
Q. Wu, Y. Zhang, S. Cui, Org. Lett., 2014, 16, 1350.
E. V. Verbitskiy, P. A. Slepukhin, Yu. O. Subbotina, M. S. Valova, A. V. Shchepochkin, E. M. Cheprakova, G. L. Rusinov, V. N. Charushin, Chem. Heterocycl. Compd. (Engl. Transl.), 2014, 50, 814 [Khim. Geterotsikl. Soedin., 2014, 883].
V. N. Charushin, H. C. van der Plas, Tetrahedron Lett., 1982, 23, 3965.
V. N. Charushin, H. C. van der Plas, Recl. Trav. Chim. PaysBas, 1983, 102, 373.
E. A. Charushin, H. C. van der Plas, Recl. Trav. Chim. PaysBas, 1974, 102, 233.
G. G. Danagulyan, Chem. Heterocycl. Compd., 2005, 41, 1205.
R. S. Sagitullin, A. N. Kost, G. G. Danagulyan, Tetrahedron Lett., 1978, 43, 4135.
G. G. Danagulyan, L. G. Sahakyan, A. R. Katritzky, S. N. Denisenko, Heterocycles, 2000, 53, 419.
B. Tao, D. W. Boykin, J. Org. Chem., 2004, 69, 4330.
E. V. Verbitskiy, E. M. Cheprakova, P. A. Slepukhin, M. I. Kodess, M. A. Ezhikova, M. G. Pervova, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, Tetrahedron, 2012, 68, 5445.
E. V. Verbitskiy, E. M. Cheprakova, E. F. Zhilina, M. I. Kodess, M. A. Ezhikova, M. G. Pervova, P. A. Slepukhin, J. O. Subbotina, A. V. Schepochkin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, Tetrahedron, 2013, 69, 5164.
G. M. Sheldrick, Acta Crystallogr., 2008, A64, 112.
WO 2011147038; Chem. Abstrs, 2011, 155, 683923.
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Dedicated to Academician of the Russian Academy of Sciences V. I. Minkin on the occasion of his 80th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0689—0694, March, 2015.
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Verbitskiy, E.V., Cheprakova, E.M., Pervova, M.G. et al. Synthesis of 6-thienyl-substituted 2-amino-3-cyanopyridines. Russ Chem Bull 64, 689–694 (2015). https://doi.org/10.1007/s11172-015-0920-8
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DOI: https://doi.org/10.1007/s11172-015-0920-8