A convergent, umpoled synthesis of 2-(1-amidoalkyl)pyridines

Abstract

A convenient, one-pot, two-component synthesis of 2-(1-amidoalkyl)pyridines is reported, based upon the substitution of suitably-activated pyridine N-oxides by azlactone nucleophiles, followed by decarboxylative azlactone ring-opening. The synthesis obviates the need for precious metal catalysts to achieve a formal enolate arylation reaction, and constitutes a formally ‘umpoled’ approach to this valuable class of bioactive structures.

Keywords

• azlactones
• pyridines
• pyridine N-oxides
• substitution