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

Author(s): Viktoriia S. Moskvina*, Olga V. Shablykina, Volodymyr P. Khilya.

Journal Name: Current Topics in Medicinal Chemistry

Volume 17 , Issue 29 , 2017

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Abstract:

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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Article Details

VOLUME: 17
ISSUE: 29
Year: 2017
Page: [3199 - 3212]
Pages: 14
DOI: 10.2174/1568026618666171227124212
Price: $58

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