Improved syntheses of substituted carbazoles and benzocarbazoles via lithiation of the (dialkylamino) methyl (aminal) derivatives

…, GW Rewcastle, LM Vazquez de Miguel

文献索引：Katritzky, Alan R.; Rewcastle, Gordon W.; Vazquez de Miguel, Luis M. Journal of Organic Chemistry, 1988 , vol. 53, # 4 p. 794 - 799

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被引用次数: 31

摘要

The lithiation of N-[(dialkylamino) methyl] carbazoles occurs readily and exclusively at the protonated carbon adjacent to the nitrogen atom. Reaction with a variety of electrophiles produces good to excellent yields of monosubstituted derivatives. Removal of the lithio- directing and nitrogen-protecting function is readily achieved by mild acid-catalyzed hydrolysis during workup of the reaction. Thus, carbazole undergoes lithiation at the 1- ...