Synthesis of new substituted imidazo[1,2-a]pyridinylpropenenitriles through sequential one-pot Suzuki–Miyaura/Knoevenagel reactions in aqueous medium

Abstract

A series of imidazo[1,2-a]pyridinylpropenenitriles were synthesized via consecutive one-pot Suzuki–Miyaura and Knoevenagel reactions in water/ethanol mixture between imidazo[1,2-a]pyridine-2-carbaldehydes, arylboronic acids and malononitrile, methyl cyanoacetate or ethyl cyanoacetate. This environmental friendly procedure tolerates a wide range of boronic acids and affords a new substituted imidazo[1,2-a]pyridinyl propenenitriles in good yields under microwave irradiation.

GRAPHICAL ABSTRACT

KEYWORDS:

• Green chemistry
• imidazo[1,2-a]pyridine
• Knoevenagel condensation
• microwave irradiation
• Suzuki–Miyaura cross-coupling

Acknowledgments

The authors thank V. Remusat for NMR spectra recording and the Spectropole team for various analytical measurements.

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

This work was supported by the Centre National de la Recherche Scientifique (CNRS), Aix-Marseille University and Houari Boumediene University of Sciences and Technology.