New reactions of hydrazides. Part 1: Directed ortho- and lateral metalation of aromatic carbocyclic and heterocyclic systems

Article abstract of DOI:10.1016/S0040-4039(99)01876-6

Aromatic and heterocyclic 2,2-dialkylhydrazides undergo directed metalation with 2 equivalents of n-, s- or t-BuLi, and the resulting C,N- dilithio species react with a variety of electrophiles. The products may be readily converted to the corresponding carboxylic acids or esters by oxidation with manganese dioxide in water or methanol containing acetic acid.