Regioselective de novo synthesis of cyanohydroxypyridines with a concerted cycloaddition mechanism.
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.
Lu
Jin-Yong
JY
Fakultät Chemie, Technische Universität Dortmund, Otto-Hahn-Strasse 6, D-44221 Dortmund, Germany.
Keith
John A
JA
Shen
Wei-Zheng
WZ
Schürmann
Markus
M
Preut
Hans
H
Jacob
Timo
T
Arndt
Hans-Dieter
HD
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
D000475:Alkenes; D001372:Aza Compounds; D003486:Cyanides; D011725:Pyridines; C014047:hydroxypyridines