通过串联过程从芳基甲基叠氮化物合成 2,4-取代的喹啉-3-羧酸乙酯。

Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process.

机构信息

Chulabhorn Research Institute, Laksi, Bangkok 10210, Thailand.

出版信息

Org Biomol Chem. 2013 Mar 7;11(9):1463-7. doi: 10.1039/c3ob27493d.

Abstract

A convenient synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters via a domino process is described. The synthesis employs arylmethyl azides as the precursor which undergoes an acid-promoted rearrangement to give an N-aryl iminium ion. Following the addition with ethyl 3-ethoxyacrylate, intramolecular electrophilic aromatic substitution, elimination and subsequent oxidation, the quinoline products were obtained in moderate to excellent yields.

摘要

通过多步反应，我们方便地合成了 2,4-取代的喹啉-3-羧酸乙酯。该合成方法采用芳基甲基叠氮化物作为前体，在酸促进下重排生成 N-芳基亚胺离子。接着与乙基 3-乙氧基丙烯酸酯进行加成反应，进行分子内亲电芳香取代、消除和随后的氧化反应，以中等至优秀的收率得到了喹啉产物。