This review highlights the promising science that has arisen from the synthesis of novel
azaheterocycles from isocoumarins. Specific topics include their synthesis and biological activity.
Isocoumarins (1H-isochromen-1-ones) are promising synthons, in particular due to the presence of
a deoxybenzoin fragment which opens up wide possibilities for synthetic transformations. The deoxybenzoin
cycle is highly susceptible to the action of various nucleophilic agents; its oxygen atom
participates in recyclization reactions under the action of N-nucleophiles where it is replaced by a
nitrogen atom, making it possible to obtain isoquinolones via a reaction with ammonia, primary
amines, hydroxylamine and benzodiazepinones via a reaction with hydrazine. We systematize literature
data, including patents (about 60 publications in all), demonstrate the routes of 3-
arylisocoumarins modification under the action of N-nucleophiles – ammonia and primary amines,
diamines, secondary amines, (het)arylamines, hydroxylamine, and hydrazines, and discuss the practical
importance of these studies for medicinal chemistry.
Keywords: Isocoumarin, 1H-isochromen-1-one, N-nucleophile, Recyclization, Ring opening ring closure reaction, Nucleophilic
reaction, Isoquinolone, Benzodiazepinone.
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