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Reactions of 3-Arylisocoumarins with N-Nucleophiles – A Route to Novel Azaheterocycles

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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.
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Keywords: 1H-isochromen-1-one; Benzodiazepinone; Isocoumarin; Isoquinolone; N-nucleophile; Nucleophilic reaction; Recyclization; Ring opening ring closure reaction

Document Type: Review Article

Publication date: November 1, 2017

This article was made available online on January 5, 2018 as a Fast Track article with title: "Reactions of 3-Arylisocoumarins with N-Nucleophiles – A Route to Novel Azaheterocycles".

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