326893-32-7Relevant academic research and scientific papers
Synthesis of 2,3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions
Aelterman,De Kimpe,Tyvorskii,Kulinkovich
, p. 53 - 58 (2007/10/03)
A new synthesis of 2,3-disubstituted pyrroles and pyridines is described. The reaction of 3-halo-1-azaallylic carbanions, regiospecifically generated from α-halogenated ketimines, with ω-iodoazides led to the regiospecific formation of ω-azido-α-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.
