title: Diversity-oriented synthesis of 1-substituted 4-aryl-6-oxo-1,6-dihydropyridine-3-carboxamides.
abstract: A simple five-step diversity-oriented synthesis of 1-substituted 4-aryl-6-oxo-1,6-dihydropyridine-3-carboxamides was developed. Treatment of dimethyl 2-((dimethylamino)methylidene)-3-oxopentanedioate with twenty primary amines gave 1-substituted methyl 4-hydroxy-6-oxo-1,6-dihydropyridine-3-carboxylates. Transformation into the corresponding 4-tosyloxy and 4-chloro derivatives, followed by Suzuki-Miyaura arylations gave a series of eleven N-substituted methyl 4-aryl-6-oxo-1,6-dihydropyridine-3-carboxylates. Combinatorial screening was employed to establish suitable reaction conditions for Suzuki-Miyaura arylation of N-alkylpyridones. Hydrolysis of the esters followed by parallel solution-phase amidation of the corresponding carboxylic acids with primary and secondary amines furnished a library of seventeen final products.
authors.affiliation: Faculty of Chemistry and Chemical Technology, University of Ljubljana , Aškerčeva 5, P.O. Box 537, 1000 Ljubljana, Slovenia.
authors.forename: Jernej
authors.initials: J
authors.lastname: Baškovč
authors.forename: Georg
authors.initials: G
authors.lastname: Dahmann
authors.forename: Amalija
authors.initials: A
authors.lastname: Golobič
authors.forename: Uroš
authors.initials: U
authors.lastname: Grošelj
authors.forename: Drago
authors.initials: D
authors.lastname: Kočar
authors.forename: Branko
authors.initials: B
authors.lastname: Stanovnik
authors.forename: Jurij
authors.initials: J
authors.lastname: Svete
mesh_terms: D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004095:Dihydropyridines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D002264:Carboxylic Acids; D004095:Dihydropyridines; C038806:1,4-dihydropyridine