ortho-Directed Lithiation Studies of 4-Chloropicolinanilide : Introduction of Functional Groups at C-3 and Their Elaboration to Chain Extended Derivatives via Carbon-Carbon Bond Formation

Authors: Dodd, R.H.; De Souza, M.V.N. Source: Heterocycles (Sendai), v. 47, p. 811, 1998. Publisher: The Japan Institute of Heterocyclic Chemistry Abstract An improved synthesis of 4-chloropicolinanilide (3) is presented. Treatment of 3 with lithium diisopropylamide (LDA) in THF, followed by addition of an electrophile (methyl iodide, iodine, carbon dioxide, trimethylstannyl chloride), gave exclusively the […]