A convenient synthesis of 2-alkyl-3-aryl-2,3-dihydro-1H-isoindol-1-ones by the reaction of N-alkyl-N-[(2-bromophenyl)methyl]benzamides with butyllithium

Add time:07/17/2019    Source:sciencedirect.com

An unprecedented and convenient synthetic approach to 2,3-dihydro-1H-isoindol-1-one (isoindolinone) derivatives has been developed. The key and final step of the method is the reaction of N-alkyl-N-(o-bromobenzyl)benzamides with butyllithium in THF at −78 °C. The corresponding 2-alkyl-3-aryl-2,3-dihydro-1H-isoindol-1-ones were produced in moderate-to-fair yields, probably via oxidation of the initially formed corresponding 2H-isoindole derivatives with air during workup.

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