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

TETRAHEDRON LETTERS

卷:53

Article

Shaw, Arthur Y.¹  Denning, Christine R.¹  Hulme, Christopher^1,2 

[1] Univ Arizona, Dept Pharmacol & Toxicol, Coll Pharm, Oro Valley BIO5, Oro Valley, AZ 85737 USA

[2] Univ Arizona, Dept Chem & Biochem, Tucson, AZ 85721 USA

关键词: alpha-Ketoamides;    Selenium dioxide;    Microwave-assisted;    Arylglyoxals;   

DOI  :  10.1016/j.tetlet.2012.05.136

来源: Elsevier

【 摘 要 】

A facile and expeditious synthetic approach for the synthesis of alpha-ketoamides 3 is described. A series of alpha-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 alpha-ketoamides 3 from various arylglyoxals 1 with cyclic and acyclic secondary amines 2. (C) 2012 Elsevier Ltd. All rights reserved.

【 授权许可】

Free