Three-Component Coupling of Aldehydes and Amines with Resorcinols and an Indole in Water without the Use of Catalysts or Promoters

Three-component coupling reactions involving aldehydes, amines, and either resorcinols or indoles are described. Substituted benzylamine derivatives were synthesized in water at room temperature. The reaction was initiated by dehydration of an aldehyde and amine, followed by arylation of the resulting imine to produce the three-component coupling product. This reaction process does not require any catalyst or promoter. The co-product is a water molecule, and the reaction proceeds under environmentally friendly conditions at room temperature in water. Substituted N-alkyl-1-(resorcinol)alkylamines and 2-arylglycines were effectively obtained in a one-pot reaction.

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Publication Details

Journal
Chemical and Pharmaceutical Bulletin
Published
2026-05-29
DOI
https://doi.org/10.1248/cpb.c26-00189
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
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article

Three-Component Coupling of Aldehydes and Amines with Resorcinols and an Indole in Water without the Use of Catalysts or Promoters

Jun’ichi Uenishi
Chemical and Pharmaceutical Bulletin
Multicomponent Synthesis of Heterocycles
article

Three-Component Coupling of Aldehydes and Amines with Resorcinols and an Indole in Water without the Use of Catalysts or Promoters

Jun’ichi Uenishi
article en

Abstract

Three-component coupling reactions involving aldehydes, amines, and either resorcinols or indoles are described. Substituted benzylamine derivatives were synthesized in water at room temperature. The reaction was initiated by dehydration of an aldehyde and amine, followed by arylation of the resulting imine to produce the three-component coupling product. This reaction process does not require any catalyst or promoter. The co-product is a water molecule, and the reaction proceeds under environmentally friendly conditions at room temperature in water. Substituted N-alkyl-1-(resorcinol)alkylamines and 2-arylglycines were effectively obtained in a one-pot reaction.

Chemical and Pharmaceutical BulletinVol. 74(5)
The University of Osaka (JP)
Clean water and sanitation
Openalex Percentile: Top 10%
Multicomponent Synthesis of Heterocycles
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