title: Regioselective de novo synthesis of cyanohydroxypyridines with a concerted cycloaddition mechanism.
abstract: An efficient cycloaddition reaction of 1-alkoxy-1-azadienes with alpha,alpha-dicyanoalkenes is described, which gives facile access to highly substituted 3-hydroxypyridines in very good yields and with complete regiocontrol and chemoselectivity. The reaction path was investigated in detail by quantum mechanics calculations, reporting that a concerted cycloaddition mechanism and thermodynamic control synergistically contribute to the observed selectivity.
authors.affiliation: Fakultät Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, D-44221 Dortmund, Germany.
authors.forename: Jin-Yong
authors.initials: JY
authors.lastname: Lu
authors.forename: John A
authors.initials: JA
authors.lastname: Keith
authors.forename: Wei-Zheng
authors.initials: WZ
authors.lastname: Shen
authors.forename: Markus
authors.initials: M
authors.lastname: Schürmann
authors.forename: Hans
authors.initials: H
authors.lastname: Preut
authors.forename: Timo
authors.initials: T
authors.lastname: Jacob
authors.forename: Hans-Dieter
authors.initials: HD
authors.lastname: Arndt
mesh_terms: D000475:Alkenes / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D008958:Models, Molecular; D015394:Molecular Structure; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D001372:Aza Compounds; D003486:Cyanides; D011725:Pyridines; C014047:hydroxypyridines