Previous Article in event
Next Article in event
Synthesis of New Bispidine-type Compounds Starting from Guareshi Imides
Published:
30 October 2012
by MDPI
in The 16th International Electronic Conference on Synthetic Organic Chemistry
session General Organic Synthesis
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
