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

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

Volume: 17 Issue: 29

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

Affiliation:

• Chemistry Department, Kyiv National Taras Shevchenko University, 12 L. Tolstogo st., Kyiv, 01033,Ukraine

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

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.

Cite this article as:

Moskvina S. Viktoriia *, Shablykina V. Olga and Khilya P. Volodymyr , Reactions of 3-Arylisocoumarins with N-Nucleophiles – A Route to Novel Azaheterocycles, Current Topics in Medicinal Chemistry 2017; 17 (29) . https://dx.doi.org/10.2174/1568026618666171227124212