An Acid-Mediated Multicomponent Domino Reaction for the Synthesis of N-Substituted Isoindolinones

This article is dedicated to Prof. H. Ila, JNCASR, Bengaluru on the occasion of her 80^th birthday. CSIR-IICT Communication no. IICT/Pubs./2024/205.

Abstract

A one-pot multicomponent reaction of 2-carboxybenzaldehyde, nitriles/anilines and a nucleophile (N,N-disubstituted anilines) for the synthesis of a range of functionalized N-substituted isoindolinone derivatives is described. This metal-free intramolecular cyclization reaction furnishes the desired products in good to excellent yields. The process is environmentally friendly and offers a sustainable method for synthesizing a diverse library of N-substituted isoindolinone derivatives under acidic conditions. This cascade reaction triggers the formation of a C–C and two C–N bonds involving carbonyl and carboxyl groups in the presence of nitriles/anilines. Additionally, in the absence of a nitrogen source, 3-substituted isobenzofuran-1(3H)-ones are synthesized.

Key words

isoindolinones - isobenzofuranones - domino reaction - multicomponent reaction - atom economy - step economy

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