Synthesis and structure of new 3,7-diazabicyclo[3.3.1]nonane derivatives


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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.

About the authors

E. A. Chigorina

State Scientific-Research Institute of Chemical Reagents and High Purity Substances (FSUE IREA)

Author for correspondence.
Email: echigorina@mail.ru
Russian Federation, 3 ul. Bogorodsky val, Moscow, 107076

K. A. Frolov

Lugansk State Medical University; ChemEx Laboratory, Vladimir Dal´ Lugansk State University

Email: echigorina@mail.ru
Ukraine, 1g kv. 50-letiya oborony, Luganska, Lugansk, 91045; Build. 7, 20a kv., Molodezhnyi, Lugansk, 91034

V. V. Dotsenko

ChemEx Laboratory, Vladimir Dal´ Lugansk State University; Kuban State University; North Caucasus Federal University

Email: echigorina@mail.ru
Ukraine, Build. 7, 20a kv., Molodezhnyi, Lugansk, 91034; 149 ul. Stavropol´skaya, Krasnodar, 350040; 1A ul. Pushkina, Stavropol´, 355009

A. S. Goloveshkin

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: echigorina@mail.ru
Russian Federation, 28 ul. Vavilova, Moscow, 119991

I. S. Bushmarinov

A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: echigorina@mail.ru
Russian Federation, 28 ul. Vavilova, Moscow, 119991

S. G. Krivokolysko

Lugansk State Medical University; ChemEx Laboratory, Vladimir Dal´ Lugansk State University

Email: echigorina@mail.ru
Ukraine, 1g kv. 50-letiya oborony, Luganska, Lugansk, 91045; Build. 7, 20a kv., Molodezhnyi, Lugansk, 91034


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