Synthesis of 2, 3-disubstituted pyrroles and pyridines from 3-halo-1-azaallylic anions

…, N De Kimpe, V Tyvorskii, O Kulinkovich

文献索引：Aelterman; De Kimpe; Tyvorskii; Kulinkovich Journal of Organic Chemistry, 2001 , vol. 66, # 1 p. 53 - 58

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被引用次数: 30

摘要

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- ...