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

doi:10.6023/cjoc201701003

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (8): 2139-2144.DOI: 10.6023/cjoc201701003 Previous Articles Next Articles

Notes

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

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 Hongli^a, Zhang Jingyuan^a, Sun Sai^a, Yang Ying^a, Zhu Xiaolei^b, Lü Chengwei^a

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).

1. N-Bromosuccinimide Mediated the Reaction of 2-Hydroxyaryl Aldehydes with Meldrum's Acid for Synthesis of Coumarin-3-carboxylic Acids.PDF(567KB)

Abstract

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

Cite this article

Ruan Hongli, Zhang Jingyuan, Sun Sai, Yang Ying, Zhu Xiaolei, Lü Chengwei. N-Bromosuccinimide Mediated the Reaction of 2-Hydroxyaryl Aldehydes with Meldrum's Acid for Synthesis of Coumarin-3-carboxylic Acids[J]. Chin. J. Org. Chem., 2017, 37(8): 2139-2144.

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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

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

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