Bromination of 7-O-Substituted-8-methyl-coumarins and 4H-Chromen-4-ones with N-Bromosuccinimide in CCl4

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (11): 1737-1741. Previous Articles Next Articles

Notes

7-O-取代-8-甲基香豆素和4H-色烯-4-酮化合物与NBS/CCl₄试剂的溴化反应

成明，裘亚，刘红山，夏鹏，陈瑛*

(复旦大学药学院上海 201203)

收稿日期:2010-01-14 修回日期:2010-05-21 发布日期:2010-06-15
通讯作者: 陈瑛 E-mail:yingchen71@fudan.edu.cn
基金资助:
国家自然科学基金

Bromination of 7-O-Substituted-8-methyl-coumarins and 4H-Chromen-4-ones with N-Bromosuccinimide in CCl₄

CHENG Ming, QIU Ya, LIU Hong-Shan, XIA Peng, CHEN Ying

(School of Pharmacy, Fudan University, ShangHai 201203)

Received:2010-01-14 Revised:2010-05-21 Published:2010-06-15

Abstract

The bromination of 7-O-substituted-8-methyl-coumarins and 4H-chromen-4-ones, two key intermediates in the synthesis of Seco-DCK and Seco-DCP analogues, with N-bromosuccinimide in CCl₄ is reported. The experimentation showed that the selectivity of bromination of 8-methyl is more complicated than that of common benzyls, due to the presence of multiple reactive sites in these two title substrates. Diversity of the products was discussed and the reasonable explanation for which was provided. The bulky group of 7-O-substitutes, its electric property as well as addition of free radical initiator could affect the selectivity and the yield of bromination of 8-methyl. The desired 8-bromomethyl products could be obtained in mild yields under optimized condition.

Key words: 7-O-substituted-8-methyl-coumarin, 7-O-substituted-8-methyl-4H-chromen-4-one, Seco-DCK, Seco-DCP, bromination

Cite this article

CHENG Ming, QIU Ya, LIU Hong-Shan, XIA Peng, CHEN Ying. Bromination of 7-O-Substituted-8-methyl-coumarins and 4H-Chromen-4-ones with N-Bromosuccinimide in CCl₄[J]. Chin. J. Org. Chem., 2010, 30(11): 1737-1741.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Siyu Mu, Hongxia Li, Zhilin Wu, Junmei Peng, Jinyang Chen, Weimin He. Electrocatalytic Three-Component Synthesis of 4-Bromopyrazoles from Acetylacetone, Hydrazine and Diethyl Bromomalonate [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4292-4299.
[2]	Mengxia Zheng, Jing Zeng, Mailikezhati Meihemuti, Abudu Rexit Abulikemu. Study on the Debromination of α-Bromomethyl Ketones Catalyzed by HBr [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2121-2126.
[3]	Li Yang, Dong Shiyu, Qin Hongwei, Tang Bingyue, Gao Wentao, Chen Yu. A Facile Synthesis and M. tuberculosis Leucyl-tRNA Synthetase Inhi-bitory Activity of Novel 3-Arylvinylquinoxaline-2-carboxylic Acids [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2817-2826.
[4]	Wang Ligeng, Yu Qin, Feng Chun, Zhang Yan, Hu Jun. Efficient Synthesis of Dibromoalkanes and Iodoacetates from Olefins Using ZnAl-XO₃^--LDHs/LiX (X=Br, I) as Halogen Sources [J]. Chin. J. Org. Chem., 2019, 39(6): 1787-1793.
[5]	Jiang Haifang, Zhang Min, Zhang Li, Chen Yali, Zhu Ning, Song Liping, Deng Hongmei. Synthesis of 3,4-Diaryl-5-aryloxymethyl Isoxazole Derivatives [J]. Chin. J. Org. Chem., 2017, 37(9): 2399-2408.
[6]	Sun Jing, Peng Xinhua, Guo Hao. Studies on Photoinduced Carbon-Silicon Bond Cleavage and Subsequent Bromination Reaction [J]. Chin. J. Org. Chem., 2015, 35(6): 1375-1379.
[7]	Li Peiyuan, Zhang Jianrui, Guo Shenghai, Zhang Xinying, Fan Xuesen. New Synthesis of Brivudine and Its Analogs [J]. Chin. J. Org. Chem., 2015, 35(4): 910-916.
[8]	Gao Wentao, Lan Shuai, Bairenqing Zhuoma, Li Yang. Convenient Synthesis 5H-[1,2,4]Triazine[5,6-b]indole-3-thiol Derivatives [J]. Chin. J. Org. Chem., 2014, 34(10): 2106-2118.
[9]	Zhang En, Li Cong, Zhang Baoyin, Lü Aiqiao, Fang Yuan, Feng Siqi, Liu Hongmin. A Practical and Efficient Synthesis of (±)-Rivastigmine [J]. Chin. J. Org. Chem., 2013, 33(05): 1100-1103.
[10]	ZHANG Guo-Fu, WANG Yong, DING Cheng-Rong, LIU Ren-Hua, LIANG Xin-Miao. Recent Advances in Oxybromination of Aromatic Compounds [J]. Chin. J. Org. Chem., 2011, 31(06): 804-813.
[11]	CHEN Zhi-Zhao, CAO De-Rong. Synthesis of Bis(4-bromo-2,5-dialkoxyphenyl)methane and Its Ana-logues [J]. Chin. J. Org. Chem., 2010, 30(11): 1742-1744.
[12]	BAN Shu-Rong, NIU Cong-Wei, CHEN Wen-Ban, LI Jing-Shan, XI Zhen. Synthesis and Bioactivity of N-(5 -Bromo-4 -substituted pyrimidin-2 -yl)phenyl Sulfonylurea [J]. Chin. J. Org. Chem., 2010, 30(04): 564-568.
[13]	SHEN Li-Tao, CHEN Gong-Biao, LIN Yuan-Bin. A New Method for α-Bromination of Methylarene [J]. Chin. J. Org. Chem., 2010, 30(02): 272-275.
[14]	ZHANG Yun-Zhi,CHEN Guan-Yu,CHEN Guo-Rong*. An Efficient Synthesis of Brominated C-Aryl Glycopyranoside [J]. Chin. J. Org. Chem., 2008, 28(2): 321-324.
[15]	WANG Dao-Lin*,XU Jiao,GU Zheng,HAN Shan. Efficient Synthesis of Methyl 3-(2-Benzo[b]furoyl)azulene- 1-carboxylates [J]. Chin. J. Org. Chem., 2007, 27(11): 1404-1408.

7-O-取代-8-甲基香豆素和4H-色烯-4-酮化合物与NBS/CCl₄试剂的溴化反应

Bromination of 7-O-Substituted-8-methyl-coumarins and 4H-Chromen-4-ones with N-Bromosuccinimide in CCl₄

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

7-O-取代-8-甲基香豆素和4H-色烯-4-酮化合物与NBS/CCl4试剂的溴化反应