Silica Gel Promotes Cascade Synthesis of 2-(Heteroaryl)acetamide Derivatives from Isocyanides, Dialkylamines, and Heteroarylcarbaldehydes

Abstract

Addition of an isocyanide to an iminium ion intermediate that forms from the reaction between a heteroarylcarbaldehyde and a secondary amine leads to formation of sterically congested 2-(heteroaryl)acetamide derivatives in the presence of silica gel at room temperature. The structures of the products were deduced from their ¹ H NMR, ¹³ C NMR, and infrared spectra and mass spectrometry.

Keywords:

• Heteroarylcarbaldehyde
• iminium ion
• isocyanide
• multicomponent reaction
• secondary amine
• silica gel

ACKNOWLEDGMENT

This work was supported by the Iranian National Science Foundation.