title: Three-step synthesis of Ethyl Canthinone-1-carboxylates from ethyl 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylate via a Pd-catalyzed Suzuki-Miyaura coupling and a Cu-catalyzed amidation reaction [corrected].
abstract: Ethyl canthin-6-one-1-carboxylate (1b) and nine analogues 1c-k were prepared from readily prepared ethyl 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylate (2b) via a three-step non-classical approach that focused on construction of the central pyrrole (ring B) using Pd-catalyzed Suzuki-Miyaura coupling followed by Cu-catalyzed C-N coupling. Furthermore, treatment of the ethyl canthinone-1-carboxylate 1b with NaOH in DCM/MeOH (9:1) gave the canthin-6-one-1-carboxylic acid (6) in high yield. All compounds are fully characterized.
authors.affiliation: Department of Chemistry, University of Cyprus, P.O. Box 20537, 1678 Nicosia, Cyprus.
authors.forename: Heraklidia A
authors.initials: HA
authors.lastname: Ioannidou
authors.forename: Aaron
authors.initials: A
authors.lastname: Martin
authors.forename: Andreas
authors.initials: A
authors.lastname: Gollner
authors.forename: Panayiotis A
authors.initials: PA
authors.lastname: Koutentis
mesh_terms: D000586:Amination; D017605:Bromine Compounds / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006868:Hydrolysis; D015394:Molecular Structure; D009287:Naphthyridines / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry*
chemical_list: D017605:Bromine Compounds; D002264:Carboxylic Acids; D009287:Naphthyridines; D010165:Palladium; D003300:Copper