Reaction of 4-Oxocyclohexane-l,l,2,2-tetracarbonitriles and 5-Hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-l,2,2-tricarbonitries with Amines

摘要

New methods have been developed for the synthesis of fused amino-substituted pyrrolidinones and dihydropyrrolones.4-Oxocyclohexane-l,l,2,2-tetracarbonitriles react with ammonia,hydrazine and hydroxylamine to give,respectively,5-amino-,5-hydrazino-,and 5-hydroxylamino-7-oxo-6-azabicyclol3.2.1J-octane-l,2,2-tricarbonitriles,while with phenylhydrazine,semicarbazide,and thiosemicarbazide,6-hydrazono-,6-semicarbazono-,and 6-thiosemicarbazono-3-amino-l-oxo-3a,4,5,6,7,7a-hexahydro-lH-isoindole-3a,7a-di-carbonitriles are formed.The latter can also be obtained under analogous conditions from 5-hydroxy-78-oxo-o-azabicyclo[3.2.1]octane-l,2,2-tricarbonitriles.Reactions of 5-hydroxy-7-oxo-6-azabicyclo[3.2.1]octane-l,2,2-tricarbonitriles with diethylamine or triethylamine give 3-amino-l,6-dioxo-3a,4,5,6,7,7a-hexanydro-1H-iso-indole-3a,7a-dicarbonitriles.