Tetrahedron p. 2055 - 2064 (1983)
Update date:2022-07-29
Topics:
Kaiser, Edwin M.
Me groups on nitrogenous heterocycles can be conveniently metallated by a variety of strongly basic reagents to afford synthetically useful carbanions.The negative charge of such anions resides predominantly on the ring N atoms.The site of lithiation on pyridines and quinolines bearing Me groups in both the 2- and 4-positions depends upon the ability of the ring N atom to complex with the metallating agents.Carbanions derived from methylated pyridines, quinolines, naphthyridines, isoquinolines, pyrido<4,3-b>carbazoles, pteridines, pyrido<3,4-b>indoles and quinoxalines are discussed.References are provided describing condensations of these reagents with a variety of both common and uncommon electrophiles.
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