2-Cyanobenzaldehye (also called 2-formylbenzonitrile) and related 2-acylbenzonitriles belong to a class of bifunctional aromatic compounds that emerged as useful starting materials in developing efficient cascade-type reactions leading to different heterocyclic compounds. The variety of sometimes unpredictable mechanisms that rise from these structurally simple starting materials renders this class of compounds unique to afford, through divergent cascade reactions, heterocycles like isoindolinones, phthalides (also known with the name of isobenzofuranones), imidates, and in less extent isoindolin-1-imine, six- and seven-membered heterocycles, porphyrins, also in asymmetric way exploiting different organocatalytic activation modes. To give a picture, this chemistry can be associated to Goldberg variations which stem from a common motive in a pressing and surprising way. In this Review, emphasis is also given to the synthetic methods for the access to substituted 2-cyanobenzaldehydes and 2-acylbenzonitriles which allowed to enlarge the scope of the described cascade reactions.

Multifaceted Behavior of 2-Cyanobenzaldehyde and 2-Acylbenzonitriles in the Synthesis of Isoindolinones, Phthalides and Related Heterocycles

Di Mola A.;Massa A.
2023-01-01

Abstract

2-Cyanobenzaldehye (also called 2-formylbenzonitrile) and related 2-acylbenzonitriles belong to a class of bifunctional aromatic compounds that emerged as useful starting materials in developing efficient cascade-type reactions leading to different heterocyclic compounds. The variety of sometimes unpredictable mechanisms that rise from these structurally simple starting materials renders this class of compounds unique to afford, through divergent cascade reactions, heterocycles like isoindolinones, phthalides (also known with the name of isobenzofuranones), imidates, and in less extent isoindolin-1-imine, six- and seven-membered heterocycles, porphyrins, also in asymmetric way exploiting different organocatalytic activation modes. To give a picture, this chemistry can be associated to Goldberg variations which stem from a common motive in a pressing and surprising way. In this Review, emphasis is also given to the synthetic methods for the access to substituted 2-cyanobenzaldehydes and 2-acylbenzonitriles which allowed to enlarge the scope of the described cascade reactions.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11386/4846052
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