A Serendipitous One-Pot Cyanation/Hydrolysis/Enamide Formation: Direct Access to 3-Methyleneisoindolin-1-ones
Trisha Banik1, Krishna P Kaliappan1
1Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India.
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.
Related Concept Videos
Aldehydes and Ketones with Amines: Enamine Formation Mechanism
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism
Aldehydes and Ketones with Amines: Imine Formation Mechanism
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...


