A regiospecific synthesis of both positional isomers of 4,6-disubstituted 2-dicyanomethylene-1, 2-dihydropyridin-3-carbonitriles.
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.
Carrión
Francisco
F
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta 390, 08017, Barcelona, Spain.
Pettersson
Sofia H
SH
Rifá
Jordi
J
Farran
Joan
J
Batllori
Xavier
X
Borrell
José I
JI
Teixidó
Jordi
J
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
D000097:Acetonitriles; D046911:Macromolecular Substances; D009570:Nitriles; D011725:Pyridines