N-SO3H functionalised brønsted acidic ionic liquid catalysed sequential one-pot synthesis of 2-amino-3-cyanopyridines via claisen-schmidt condensation under solvent-free condition

TitleN-SO3H functionalised brønsted acidic ionic liquid catalysed sequential one-pot synthesis of 2-amino-3-cyanopyridines via claisen-schmidt condensation under solvent-free condition
Publication TypeJournal Article
Year of Publication2024
AuthorsDas, S, Paul, S, Kashyap, N, Saikia, P, Borah, R
JournalChemistryselect
Volume9
Issue11
Date PublishedMAR
Type of ArticleArticle
ISSN2365-6549
Keywords2-amino-3-cyanopyridines, Bronsted acidic ionic liquids, chalcones, Multicomponent reaction, One-pot approach
Abstract

This work presents a simple approach for the synthesis of 2-amino-3-cyanopyridines via a one pot two-step sequential route catalysed by direct N–SO3H functionalised Br & oslash;nsted acidic ionic liquids (BAILs). Herein, catalytic activities of four BAILs namely ([TSPi][Cl](2), [DSIM][TFA], [EDSIM][TFA] and [DBDSA][TFA]) were explored and among them [TSPi][Cl](2) was found to be the most efficient reusable homogeneous catalyst. This process involves the ionic liquid catalysed in situ generation of chalcones from Claisen-Schmidt condensation between aromatic aldehydes and acetophenone/4-Cl acetophenone, followed by multicomponent reaction (MCR) with malononitrile and ammonium acetate using the same IL catalyst to selectively produce 2-amino-3-cyanopyridine derivatives in a solvent-free medium at 80 degrees C within 30-60 minutes in high yields (96-86 %). This amalgamation of MCR with ionic liquids and solvent-free conditions makes the present work more compliant with the protocols of Green Chemistry.

DOI10.1002/slct.202304103
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

2.1

Divison category: 
Organic Chemistry
Database: 
Web of Science (WoS)

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