2-(2-苯并呋喃基)-6-氯-3-喹啉甲酸衍生物的简便合成
收稿日期: 2016-04-28
修回日期: 2016-07-12
网络出版日期: 2016-08-10
基金资助
国家自然科学基金（Nos. 21476028，21402011）资助项目.
A Facile Synthesis of 2-(Benzofuran-2-yl)-6-chloroquinoline-3-carboxylic Acid Derivatives
Received date: 2016-04-28
Revised date: 2016-07-12
Online published: 2016-08-10
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21476028, 21402011).
以6-氯-2-氯甲基-3-喹啉甲酸乙酯（1）为底物，在无水碳酸钾作为缚酸剂、乙腈作为溶剂、聚乙二醇-400作为相转移催化剂的条件下分别与水杨醛（2a~2i）、邻羟基苯乙酮（2j~2o）及2-羟基-1-萘醛（2p）经“三步一锅法”在超声辅助下回流反应，成功的合成了2-（2-苯（萘）并呋喃基）-6-氯-3-喹啉甲酸衍生物（3a~3p）.所合成化合物的结构均通过红外光谱、核磁共振氢谱、核磁共振碳谱和高分辨质谱得以证实.
关键词： 6-氯-2-氯甲基-3-喹啉甲酸乙酯; 苯(萘)并呋喃; 聚乙二醇-400; 超声波辅助; 三步一锅法
高文涛 , 符鑫博 , 李阳 , 王东方 , 赵雅楠 . 2-(2-苯并呋喃基)-6-氯-3-喹啉甲酸衍生物的简便合成[J]. 有机化学, 2016 , 36(12) : 2965 -2972 . DOI: 10.6023/cjoc201604058
A facile synthesis of 2-(benzo(naphtho)furan-2-yl)-6-chloroquinoline-3-carboxylic acid derivatives (3a~p) has been described, involving ultrasound-assisted three-step one-pot reaction of ethyl 6-chloro-2-(chloromethyl)quinoline-3-carboxylate (1) with corresponding salicylaldehydes (2a~2i), 1-(2-hydroxyphenyl)ethanones (2j~2o) or 2-hydroxy-1-naphthaldehyde (2p) in the presence of K2CO3 as acid-binding agent and PEG-400 as phase transfer catalyst in refluxing MeCN. The synthesized compounds were new, and their structures had been determined by IR, 1H NMR, 13C NMR and HRMS.
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