Selenium dioxide-mediated synthesis of α-ketoamides from arylglyoxals and secondary amines

Tetrahedron Lett. 2012 Aug 8;53(32):4151-4153. doi: 10.1016/j.tetlet.2012.05.136. Epub 2012 Jun 6.

Abstract

A facile and expeditious synthetic approach to α-ketoamides 3 is described. A series of α-ketoamides 3 was synthesized via reaction of selenium dioxide-mediated oxidative amidation between arylglyoxals 1 and secondary amines 2, and accelerated with microwave irradiation. Our findings indicate that constrained amines, such as piperazine and piperidine exhibit higher conversions for this transformation. This reaction was explored by synthesizing a series of α-ketoamides 3 from various arylglyoxals with cyclic and acyclic secondary amines.