Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions.
A new synthesis of 2,3-disubstituted pyrroles and pyridines is described. The reaction of 3-halo-1-azaallylic carbanions, regiospecifically generated from alpha-halogenated ketimines, with omega-iodoazides led to the regiospecific formation of omega-azido-alpha-haloketimines. Treatment of these functionalized imines with tin(II) chloride afforded halogenated five- and six-membered cyclic imines, which were transformed under mild conditions into 2,3-disubstituted pyrroles and pyridines. The stereoselective reduction of 2,3-dialkyl-3-chloro-1-pyrrolines to afford cis-2,3-dialkyl-3-chloropyrrolidines is also reported.
Aelterman
W
W
Department of Organic Chemistry, Faculty of Agricultural and Applied Biological Sciences, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
De Kimpe
N
N
Tyvorskii
V
V
Kulinkovich
O
O