O. V. Ershov, V. P. Sheverdov, O. Nasakin
Oct 1, 2001
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0
Influential Citations
3
Citations
Journal
Russian Journal of Organic Chemistry
Abstract
We reported formerly on the synthesis of 5-hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-1,2,2-tricarbonitriles (Ia3f) from tetracyanoethylene and appropriate a,b-unsaturated ketones [1, 2]. We found that at treating the azabicyclic compounds Ia3f with various bases, in particular amines, pyrrolidine ring underwent opening yielding 5-oxo-1,2,2-tricyano-1-cyclohexanecarboxamides ( IIa 3d) that furthercyclized into 3-amino-1,6-dioxo-3a,4,5,6,7,7a-hexahydro-1H-isoindole-3a,7a-dicarbonitriles ( IIIa 3f). The conversion is affected by the reaction temperature and amount of the base brought intoreaction. The use of equimolar quantity of sodium alcoholate in the corresponding alcohol at room temperature led to heterolytic cleavage of the N3C bond in azabicyclic compounds Ia3f to afford carboxamidesIIa 3d. At heating aza-