Journal of Organic Chemistry p. 794 - 799 (1988)
Update date:2022-08-05
Topics:
Katritzky, Alan R.
Rewcastle, Gordon W.
Vazquez de Miguel, Luis M.
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-position, dibenzo
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