A Serendipitous One-Pot Cyanation/Hydrolysis/Enamide Formation: Direct Access to 3-Methyleneisoindolin-1-ones

Chemistry. 2021 Jan 7;27(2):628-633. doi: 10.1002/chem.202003209. Epub 2020 Dec 3.

Abstract

A direct, one-pot conversion of 2'-haloacetophenones to 3-methyleneisoindolin-1-one scaffolds using CuCN as the sole reagent without the need for moisture-free or anaerobic conditions is reported. This serendipitously discovered transformation with a broad substrate scope provides a significantly different route towards these important scaffolds. The scope of the method has also been further extended towards the synthesis of three special scaffolds, which are analogous to various bio-active drugs.

Keywords: 3-methyleneisoindolin-1-one; cyanation; enamide formation; heterocycles; one-pot transformation.