Canadian journal of chemistry

Concerning the mechanism of the Friedländer quinoline synthesis

JM Muchowski, ML Maddox

Index: Muchowski, Joseph M.; Maddox, Michael L. Canadian Journal of Chemistry, 2004 , vol. 82, # 3 p. 461 - 478

Full Text: HTML

Citation Number: 52

Abstract

Detailed experiments regarding the mechanism of the Friedländer synthesis of quinolines from o-aminobenzaldehydes and simple aldehydes or ketones are described. Under the basic or acidic conditions commonly used in this reaction, it is concluded that the first step involves a slow intermolecular aldol condensation of the aldehyde or ketone with the o- aminobenzaldehyde. The aldol adduct 5 generated in this manner then undergoes very ...