An Expedient Method for Regioselective Methylation of Catechol Coumarins

doi:10.1007/s40242-016-6147-x

Chemical Research in Chinese Universities ›› 2016, Vol. 32 ›› Issue (5): 786-791.doi: 10.1007/s40242-016-6147-x

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An Expedient Method for Regioselective Methylation of Catechol Coumarins

LU Junxia^1,3, WANG Ping³, HOU Jie⁴, ZOU Liwei³, CUI Pan³, YANG Ling³, GE Guangbo³, GONG Xiaojie²

1. College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. China;
2. College of Medical, Dalian University, Dalian 116622, P. R. China;
3. Laboratory of Pharmaceutical Resource Discovery, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian 116023, P. R. China;
4. College of Basic Medical Sciences, Dalian Medical University, Dalian 116044, P. R. China

Received:2016-04-15 Revised:2016-06-02 Online:2016-10-01 Published:2016-09-24
Contact: GE Guangbo, GONG Xiaojie E-mail:gxjclr@163.com;geguangbo@dicp.ac.cn
Supported by:
Supported by the National Basic Research Program of China(No.2013CB531800), the National Natural Science Foundation of China(Nos.81402822, 81302793) and the Science and Technology Project of Liaoning Province of China(No.2014204007).

Abstract

Abstract:

An expedient and efficient method for selective methylation of catechol coumarins by working with different alkalis under appropriate reaction conditions was reported. Esculetins were selectively methylated at position 6 and position 7 in good yields using CH₃I in the presence of NaH and Na₂CO₃, respectively. However, daphnetins showed less regioselectivity under the same reaction conditions. Furthermore, the site preference for the methylation reaction was interpreted by the density functional theory at B3LYP/6-31+G(d) level.

Key words: Catechol coumarin, Regioselective methylation, Density functional theory

LU Junxia, WANG Ping, HOU Jie, ZOU Liwei, CUI Pan, YANG Ling, GE Guangbo, GONG Xiaojie. An Expedient Method for Regioselective Methylation of Catechol Coumarins[J]. Chemical Research in Chinese Universities, 2016, 32(5): 786-791.

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An Expedient Method for Regioselective Methylation of Catechol Coumarins

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