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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 10
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Original Articles

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

, , , , , , , , , , , , & show all
Pages 1444-1454 | Received 21 Nov 2009, Published online: 30 Mar 2011
 

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 Citation 1 H NMR, Citation 13 C NMR, and infrared spectra and mass spectrometry.

ACKNOWLEDGMENT

This work was supported by the Iranian National Science Foundation.

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