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Synthesis of New Bispidine-type Compounds Starting from Guareshi Imides
* 1 , 2
1  ChemDiv Research Institute (CDRI), Rabochaya St. 2-a, Moscow Region, Khimki
2  ChemEx Laboratory, Vladimir Dal' East Ukrainian Nationa University, Molodezhny 20A, Lugansk

Abstract: The reaction of 1-cyanoacetyl-3,5-dimethylpyrazole with 2-cyanoacrylamides in the presence of triethylamine leads to triethylammonium 3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-olates (salts of Guareshi imides). The latter reacted with primary amines RNH2 and excessive HCHO to give triethylammonium salts of 7-R-2,4-dioxo-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarbonitriles. When treated with HCl or alkyl halides, the salts afforded corresponding 3-R- or 3,7-disubstituted bispidines.
Keywords: cyanoacetylpyrazole, Guareshi imides, diazabicyclononanes, bispidines,Mannich reaction