2-氯甲基-4-甲基-3-喹啉甲酸乙酯与酚的反应研究

Study on the reaction of ethyl 2-(chloromethyl)-4-methylquinoline-3-carboxylate with phenols

本文以2-氯甲基-4-甲基-3-喹啉甲酸乙酯(1)为底物,在溶剂乙腈、催化剂无水碳酸钾的条件下,与各种取代的酚2a-l和二酚2m-q反应经"一锅法"合成了4-甲基-2-芳氧甲基-3-喹啉甲酸衍生物3a-l,5a-e,其收率为54.6-92.1%.化合物3a-l在闭环试剂PPA的作用下发生闭环反应得到氧杂并喹啉酮类化合物4a-l,其收率为53.1-84.8%.化合物3a-l,4a-l,5a-e为新化合物,其结构经IR、~1H NMR、^(13)C NMR和HR-MS得以确定.

In the present investigation,ethyl 2-（ chloromethyl）-4-methylquinoline-3-carboxylate（ 1） was used as raw material to react with various phenols（ 2a-l） and diphenols（ 2m-q） in the presence of potassium carbonate as catalyst in refluxing acetonitrile to give4-methyl-2-（ aryloxymethyl） quinolin-3-carboxylic acid derivatives 3a-l,5a-e with yields ranging 54. 6-92. 1%. Further,compounds3a-l underwent the intramolecular acylation reaction in polyphosphoric acid（ PPA） to obtain polycyclic-fused quinolines 4a-l with yields ranging 53. 1-84. 8%. The synthesized compounds 3a-l,4a-l and 5a-e were new,and their structures had been determined by IR,~1H NMR,13C NMR and HR-MS.