Meinwald-Friedlnder反应合成3-芳基取代喹啉

Synthesis of 3-Aryl Substituted Quinolines by Meinwald-Friedlnder Reaction

用三氟甲磺酸(TfOH,5 mol%)催化查尔酮环氧化物(1a～1j)在氯苯中开环-重排,然后KOBut作碱与邻氨基苯甲醛通过Meinwald-Friedlnder反应,"一锅"合成了3-芳基取代喹啉,收率51%～74%。TfOH(5mol%)催化1在二氯甲烷中发生Meinwald重排,生成相应的开环产物3-氧代-2,3-二芳基丙醛,收率48%～89%。化合物的结构经NMR和MS确证。

3-Aryl substituted quinolines in yields of 51%~74% were sythesized by ＂one-pot＂ method using trifluoromethanesulfonic acid（TfOH,5 mol%） as the catalyst in chlorobenzene from chalcone epoxide（1） by ring-opening-rearrangement reaction,then by Meinwald-Friedlnder reaction with o-aminobenzaldehyde in the presence of KOBut.3-Oxo-2,3-diarylpropionaldehydes in yields of 48%~89% were prepared by Meinwald rearrangement reaction of 1 using TfOH（5 mol%） as the catalyst in methylene chloride.The structures were confirmed by NMR and MS.