有机化学 ›› 2017, Vol. 37 ›› Issue (8): 2139-2144.DOI: 10.6023/cjoc201701003 上一篇    下一篇

研究简报

N-溴代丁二酰亚胺催化水杨醛与麦氏酸反应合成香豆素-3-羧酸

阮鸿力a, 张婧圆a, 孙赛a, 杨颖a, 朱小磊b, 吕成伟a   

  1. a 辽宁师范大学化学化工学院 大连 116029;
    b 鞍山市教师进修学校 鞍山 14000
  • 收稿日期:2017-01-05 修回日期:2017-03-21 发布日期:2017-04-18
  • 通讯作者: 吕成伟 E-mail:chengweilv@126.com
  • 基金资助:

    国家自然科学基金(No.21403100)和辽宁省博士启动基金(No.20141100)资助项目.

N-Bromosuccinimide Mediated the Reaction of 2-Hydroxyaryl Aldehydes with Meldrum's Acid for Synthesis of Coumarin-3-carboxylic Acids

Ruan Honglia, Zhang Jingyuana, Sun Saia, Yang Yinga, Zhu Xiaoleib, Lü Chengweia   

  1. a School of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
    b Teachers Training College of Anshan, Anshan 114000
  • Received:2017-01-05 Revised:2017-03-21 Published:2017-04-18
  • Contact: 10.6023/cjoc201701003 E-mail:chengweilv@126.com
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21403100) and the Doctoral Scientific Research Foundation of Liaoning Province (No. 20141100).

室温条件下、水和乙醇的混合液中,N-溴代丁二酰亚胺(NBS)促进2-羟基苯甲醛与麦氏酸连续发生Knoevenagel缩合反应和分子内环化反应,高产率地合成了一系列的香豆素-3-羧酸.该方法扩展了可用于合成香豆素-3-羧酸的催化剂的种类,同时还具有催化剂廉价易得、反应条件清洁环保、底物适用性广、后处理简单和产物易于纯化等优点.

关键词: N-溴代丁二酰亚胺, 香豆素-3-羧酸, 合成方法, 室温, 绿色化学

A N-bromosuccinimide (NBS) promoted procedure for the synthesis of coumarin-3-carboxylic acids via Knoevenagel-intramolecular cyclization cascade reaction of Meldrum's acid with various 2-hydroxyarylaldehydes has been developed. Using the mixture of water and ethanol as solvent, employing inexpensive NBS as the catalyst, and reacted at room temperature are found to highly applicable to get a satisfactory outcome. This approach expands the method for the preparation of coumarin-3-carboxylic acids and also provides other features such as mild reaction conditions, tolerant the substrates with diverse functional groups, simple workup procedure and easy isolation.

Key words: N-bromosuccinimide, coumarin-33-carboxylic acids, synthetic methods, room temperature, green chemistry