Abstract
Aminomethylation of triethylammonium 4-aryl-3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridin-2-olates and their sulfur and selenium analogs, as well as the structure of formed products, were studied in details. The reaction is of general character and leads to the formation of 7-substituted 9-aryl-2,4-dioxo-, 9-aryl-4-oxo-2-thioxo-, 9-aryl-4-oxo-2-selenoxo-3,7-diazabicyclo[3.3.1]nonane derivatives or their salts. The structures of ethyl 9-(2-chlorophenyl)-5-cyano-7-(4-methylphenyl)-2-oxo-4-thioxo-3,7-diazabicyclo[3.3.1]nonane-1-carboxylate (as a complex with N-methylmorpholine) and triethylammonium salt of 7-benzyl-4-oxo-2-selenoxo-9-(2-thienyl)-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarbonitrile were studied by X-ray crystallography.
Similar content being viewed by others
References
N. S. Zefirov, S. V. Rogozina, Russ. Chem. Rev., 1973, 42, 190.
R. Jeyaraman, S. Avila, Chem. Rev., 1981, 81, 149.
N. S. Zefirov, V. A. Palyulin, Top. Stereochem., 1991, 20, 171.
G. L. Garrison, K. D. Berlin, B. J. Scherlag, R. Lazzara, E. Patterson, T. Fazekas, S. Sangiah, C. L. Chen, F. D. Schubot, D. van der Helm, J. Med. Chem., 1996, 39, 2559.
G. S. Smith, M. D. Thompson, K. D. Berlin, E. M. Holt, B. J. Scherlag, E. Patterson, R. Lazzara, Eur. J. Med. Chem., 1990, 25, 1.
B. Kцgel, T. Christoph, E. Fridericks, H. H. Hennies, T. Mathiesen, J. Schneider, U. Holzgrabe, CNS Drug Rev., 1998, 4, 54
U. Kuhl, W. Englberger, M. Haurand, U. Holzgrabe, Arch. Pharm., 2000, 333, 226
T. Siener, A. Cambareri, U. Kuhl, W. Englberger, M. Haurand, B. Kögel, U. Holzgrabe, J. Med. Chem., 2000, 43, 3746
U. Kuhl, M. von Korff, K. Baumann, C. Burschka, U. Holzgrade, J. Chem. Soc., Perkin Trans. 2, 2001, 2037
U. Holzgrabe, W. Brandt, J. Med. Chem., 2003, 46, 1383
Y. Wang, K. Tang, S. Inan, D. Siebert, U. Holzgrabe, D. Y. W. Lee, P. Huang, J.-G. Li, A. Cowan, L.-Y. Liu-Chen, J. Pharmacol. Exp. Therap., 2005, 312, 220.
S. Z. Vatsadze, V. S. Tyurin, N. V. Zyk, A. V. Churakov, L. G. Kuz´mina, E. V. Avtomonov, R. D. Rakhimov, K. P. Butin, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 1825 [Izv. Akad. Nauk, Ser. Khim., 2005, 1773]
P. Comba, H. Pritzkow, W. Schiek, Angew. Chem., Int. Ed., 2001, 40, 2465.
P. Comba, B. Nuber, A. Ramlow, J. Chem. Soc. Dalton Trans., 1997, 347.
P. Comba, B. Kanellakopulos, Ch. Katsichtis, A. Lienke, H. Pritzkow, F. Rominger, J. Chem. Soc. Dalton Trans., 1998, 3997.
D. St. C. Black, G. B. Deacon, M. Rose, Tetrahedron, 1995, 51, 2005.
M. R. Bukowski, P. Comba, A. Lienke, C. Limberg, C. Lopez de Laorden, R. Mas-Ballestй, M. Merz, L. Que, Angew. Chem., Int. Ed., 2006, 45, 3446.
M. Haberberger, C. I. Someya, A. Company, E. Irran, S. Enthaler, Catalysis Lett., 2012, 142, 557.
P. Comba, Y.-M. Lee, W. Namb, A. Waleska, Chem. Commun., 2014, 50, 412.
E. A. Chigorina, V. V. Dotsenko, Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 48, 1722 [Khim. Geterotsikl. Soedin., 2012, 1838].
V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Chem. Heterocycl. Compd. (Engl. Transl.), 2005, 41, 1428 [Khim. Geterotsikl. Soedin., 2005, 1695].
V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Monatsh. Chem., 2007, 138, 489.
V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Russ. Chem. Bull. (Int. Ed.), 2007, 56, 2482 [Izv. Akad. Nauk, Ser. Khim., 2007, 2397].
V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Chem. Heterocycl. Compd. (Engl. Transl.), 2015, 51, 109 [Khim. Geterotsikl. Soedin., 2015, 51, 109].
V. V. Dotsenko, K. A. Frolov, S. G. Krivokolysko, Chem. Heterocycl. Compd. (Engl. Transl.), 2013, 49, 657 [Khim. Geterotsikl. Soedin., 2013, 705].
K. A. Frolov, V. V. Dotsenko, S. G. Krivokolysko, V. P. Litvinov, Chem. Heterocycl. Compd. (Engl. Transl.), 2012, 48, 442 [Khim. Geterotsikl. Soedin., 2012, 471].
Structure Correlation, Eds H.-B. Burgi, J. D. Dunitz, Verlag Chemie, Weinheim, 1994, Vol. 2, p. 741.
V. V. Dotsenko, K. A. Frolov, S. G. Krivokolysko, E. A. Chigorina, T. M. Pekhtereva, S. Yu. Suykov, E. S. Papayanina, A. O. Dmitrienko, I. S. Bushmarinov, Chem. Heterocycl. Compd. (Engl. Transl.), 2016, 52, 116 [Khim. Geterotsikl. Soedin., 2016, 52, 116].
E. A. Chigorina, V. V. Dotsenko, S. G. Krivokolysko, Chem. Heterocycl. Compd. (Engl. Transl.), 2011, 47, 913 [Khim. Geterotsikl. Soedin., 2011, 1108]
E. A. Chigorina, Chem. Heterocycl. Compd. (Engl. Transl.), 2013, 49, 574 [Khim. Geterotsikl. Soedin., 2013, 615].
V. D. Dyachenko, Yu. A. Sharanin, S. G. Krivokolysko, Russ. J. Org. Chem. (Engl. Transl.), 1995, 31, 136 [Zh. Org. Khim., 1995, 31, 149]
S. G. Krivokolysko, V. D. Dyachenko, V. N. Nesterov, Yu. A. Sharanin, Yu. T. Struchkov, Zh. Org. Khim., 1999, 35, 966 [Russ. J. Org. Chem. (Engl. Transl.), 1999, 35]
S. G. Krivokolysko, V. D. Dyachenko, V. P. Litvinov, Russ. Chem. Bull. (Int. Ed.), 2000, 49, 487 [Izv. Akad. Nauk, Ser. Khim., 2000, 485].
G. Sheldrick, Acta Cryst. Sect. A, 2008, 64, 112.
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, H. Puschmann, J. Appl. Cryst., 2009, 42, 339.
Author information
Authors and Affiliations
Corresponding author
Additional information
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 2260—2269, September, 2016.
Rights and permissions
About this article
Cite this article
Chigorina, E.A., Frolov, K.A., Dotsenko, V.V. et al. Synthesis and structure of new 3,7-diazabicyclo[3.3.1]nonane derivatives. Russ Chem Bull 65, 2260–2269 (2016). https://doi.org/10.1007/s11172-016-1576-8
Received:
Revised:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11172-016-1576-8