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

Sudheer Kumar Karu; Meghanath Veludandi; Chandrasekharam Malapaka

doi:10.1055/a-2380-9676

Synthesis, Table of Contents

Synthesis 2025; 57(02): 417-424
DOI: 10.1055/a-2380-9676

paper

Special Topic Dedicated to Prof. H. Ila

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

Sudheer Kumar Karu∗

^aPolymers & Functional Materials Dept., CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

,

Meghanath Veludandi

^aPolymers & Functional Materials Dept., CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India

,

Chandrasekharam Malapaka∗

^aPolymers & Functional Materials Dept., CSIR-Indian Institute of Chemical Technology, Hyderabad, 500 007, India

^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

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Abstract

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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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References

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