A concise and regioselective synthesis of 1-alkyl-4-imidazolecarboxylates.
Reaction between ethyl 3-N,N-(dimethylamino)-2-isocyanoacrylate (1) and a primary amine (2) regioselectively affords 1-alkyl-4-imidazolecarboxylates (3) in good yields (52-89%). The method is applicable to unhindered and hindered amine substrates, as well as those containing reactive functionality such as alcohols and secondary and tertiary amines. [reaction: see text]
Helal
Christopher J
CJ
Neuroscience Medicinal Chemistry, Pfizer Global Research and Development, Eastern Point Road, Groton, CT 06340, USA. chris_j_helal@groton.pfizer.com
Lucas
John C
JC
D000478:Alkylation; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D007093:Imidazoles / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D002264:Carboxylic Acids; D007093:Imidazoles; D007202:Indicators and Reagents