title: Direct Synthesis of 5-Aryl Barbituric Acids by Rhodium(II)-Catalyzed Reactions of Arenes with Diazo Compounds.
abstract: A commercially available rhodium(II) complex catalyzes the direct arylation of 5-diazobarbituric acids with arenes, allowing straightforward access to 5-aryl barbituric acids. Free N-H groups are tolerated on the barbituric acid, with no complications arising from N-H insertion processes. This method was applied to the concise synthesis of a potent matrix metalloproteinase (MMP) inhibitor.
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD (UK).
authors.forename: Daniel
authors.initials: D
authors.lastname: Best
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD (UK).
authors.forename: David J
authors.initials: DJ
authors.lastname: Burns
authors.affiliation: School of Chemistry, University of Nottingham, University Park, Nottingham, NG7 2RD (UK). hon.lam@nottingham.ac.uk.
authors.forename: Hon Wai
authors.initials: HW
authors.lastname: Lam
mesh_terms: D001391:Azo Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D001463:Barbiturates / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D061965:Matrix Metalloproteinase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D001463:Barbiturates; D006841:Hydrocarbons, Aromatic; D061965:Matrix Metalloproteinase Inhibitors; D012238:Rhodium; C032232:barbituric acid
keywords: arylation; barbituric acid; carbenes; diazo compounds; rhodium