title: A regiospecific synthesis of both positional isomers of 4,6-disubstituted 2-dicyanomethylene-1, 2-dihydropyridin-3-carbonitriles.
abstract: A protocol allowing the regiospecific synthesis of both positional isomers of 4,6-disubstituted 2-dicyanomethylene-1,2-dihydropyridin-3-carbonitriles, precursors of 1,6-naphthyridines, is presented. Thus, treatment of enaminoketones with the propanedinitrile dimer yields one regioisomer while the treatment of the corresponding (3-chloro-allylidene)-dimethylammonium perchlorates (easily obtained from enaminoketones and POCl(3)), in which the nature of the reactive centers is inverted with respect to the enaminoketone, yields the other regioisomer.
authors.affiliation: Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta 390, 08017, Barcelona, Spain.
authors.forename: Francisco
authors.initials: F
authors.lastname: Carrión
authors.forename: Sofia H
authors.initials: SH
authors.lastname: Pettersson
authors.forename: Jordi
authors.initials: J
authors.lastname: Rifá
authors.forename: Joan
authors.initials: J
authors.lastname: Farran
authors.forename: Xavier
authors.initials: X
authors.lastname: Batllori
authors.forename: José I
authors.initials: JI
authors.lastname: Borrell
authors.forename: Jordi
authors.initials: J
authors.lastname: Teixidó
mesh_terms: D000097:Acetonitriles / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D046911:Macromolecular Substances / Q000138:chemical synthesis / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008954:Models, Biological; D008958:Models, Molecular; D008968:Molecular Conformation; D009570:Nitriles / Q000138:chemical synthesis* / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000097:Acetonitriles; D046911:Macromolecular Substances; D009570:Nitriles; D011725:Pyridines