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 α-halogenated ketimines, with ω-iodoazides led to the regiospecific formation of ω-azido-α-haloketimines. Treatment of these functionalized imine...

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Veröffentlicht in:Journal of organic chemistry 2001-01, Vol.66 (1), p.53-58
Hauptverfasser: Aelterman, Wim, De Kimpe, Norbert, Tyvorskii, Vladimir, Kulinkovich, Oleg
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo000724t