Recent advances in the friedländer reaction

A study was conducted to demonstrate the latest advancements in the Friedländer reaction. The Friedländer reaction involved a complex series of events where competing mechanistic pathways occurred depending on structure of reactions and reaction conditions. A modified Friedländer quinoline synthesis process was introduced that proceeded in the presence of KOH, iridium(III), ruthenium, rhodium, palladium, on charcoal or copper(II) catalyst. The reaction proceeded through consecutive oxidation of 2-amino benzyl alcohol to the corresponding 2-amino acetaldehyde, followed by coupling with the ketones added to the reaction medium or obtained in situ by oxidation of the alcohol under existing experimental conditions. Another new method was also successfully applied for the preparation of naphthyridines and 2,3,5-trisubstituted quinolines involving lithiation of N-pivaloylanilines with s-BuLi.