Recent advances in the friedländer reaction

José Marco-Contelles, Elena Pérez-Mayoral, Samadi Abdelouahid Samadi, María Do Carmo Carreiras, Elena Soriano

Research output: Contribution to journalArticlepeer-review

540 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2652-2671
Number of pages20
JournalChemical Reviews
Volume109
Issue number6
DOIs
Publication statusPublished - Jun 10 2009
Externally publishedYes

ASJC Scopus subject areas

  • Chemistry(all)

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