Heterocyclic carbanions. Synthesis of 2-substituted imidazole and benzimidazoles and of 3-substituted pyrazoles by lithiation of N-(dialkylamino) methyl heterocycles

AR Katritzky, GW Rewcastle…

文献索引：Katritzky, Alan R.; Rewcastle, Gordon W.; Fan, Wei-Qiang Journal of Organic Chemistry, 1988 , vol. 53, # 24 p. 5685 - 5689

全文：HTML全文

被引用次数: 46

摘要

The lithiation of N-(dialky1amino) methyl (aminal) derivatives of imidazole, benzimidazole, and pyrazole (themselves readily available from the parent heterocycles, formaldehyde, and a secondary amine) occurs smoothly at the 2-, 2-, and 5-positions, respectively, upon treatment with n-butyllithium in ether or tetrahydrofuran. Reaction with electrophiles, and subsequent facile acid-catalyzed hydrolysis of the protecting group, provides 2-substituted ...