title: A concise and regioselective synthesis of 1-alkyl-4-imidazolecarboxylates.
abstract: 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]
authors.affiliation: Neuroscience Medicinal Chemistry, Pfizer Global Research and Development, Eastern Point Road, Groton, CT 06340, USA. chris_j_helal@groton.pfizer.com
authors.forename: Christopher J
authors.initials: CJ
authors.lastname: Helal
authors.forename: John C
authors.initials: JC
authors.lastname: Lucas
mesh_terms: D000478:Alkylation; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D007093:Imidazoles / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D002264:Carboxylic Acids; D007093:Imidazoles; D007202:Indicators and Reagents