Intramolecular nucleophilic aromatic substitution reactions involving the novel displacement of hydride ion by cyanobenzyl carbanions
Abstract
α-(N-Substituted-N-3,5-dinitrobenzoylamino)-, α-(N-substituted-N-2-chloro-3,5-dinitrobenzoylamino)-, and α-(N-substituted-N-3-nitrobenzoylamino)phenylacetonitriles (1) and (2) undergo base-catalysed cyclisation with displacement of hydride ion or chloride ion to afford the corresponding isoindolin-1-ones (3), (4), and (5).