Abstract:The azaphthalimide 2a is the first phthalimide oxygen found to undergo a neighboring‐group participation reaction with a vicinal N‐phenyl carboxylic acid chloride upon nucleophilic addition with alcohols. Owing to the free rotation of the N‐phenyl moiety, hetero‐anellated benzoxazinedione isomers 3 and 4 are accessible, whereby 3 is preferred to 4 as the pyridine nitrogen in 2a preferentially activates the o‐carbonyl group. Yields of up to 92% were obtained when bases such as HCl acceptors were avoided by heat… Show more
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