Efficient synthesis of imidazoles from aldehydes and 1,2-diketones using microwave irradiation.
[reaction: see text] A simple, high-yielding synthesis of 2,4,5-trisubstituted imidazoles from 1,2-diketones and aldehydes in the presence of NH(4)OAc is described. Under microwave irradiation, alkyl-, aryl-, and heteroaryl-substituted imidazoles are formed in yields ranging from 80 to 99%. Short syntheses of lepidiline B and trifenagrel illustrate the utility of this approach.
Wolkenberg
Scott E
SE
Department of Medicinal Chemistry, Technology Enabled Synthesis Group, Merck Research Laboratories, P.O. Box 4, West Point, Pennsylvania 19486, USA. scott_wolkenberg@merck.com
Wisnoski
David D
DD
Leister
William H
WH
Wang
Yi
Y
Zhao
Zhijian
Z
Lindsley
Craig W
CW
D000447:Aldehydes / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D007093:Imidazoles / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry* / Q000528:radiation effects; D008872:Microwaves; D015394:Molecular Structure
D000447:Aldehydes; D007093:Imidazoles; D007659:Ketones; C059718:trifenagrel