A Clean Synthesis of 1,4-Diarylquinoline-2,5-dione Derivatives in Aqueous Media

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (11): 1811-1815. Previous Articles Next Articles

Full Papers

水介质中1,4-二芳基喹啉-2,5-二酮衍生物的绿色合成

张梅梅^a 李庆^b 吴健蓉^b 王香善^*,a,b

(a徐州师范大学江苏省药用植物生物技术重点实验室徐州 221116) (b徐州师范大学化学化工学院徐州221116)

收稿日期:2009-02-22 修回日期:2009-05-21 发布日期:2009-06-26
通讯作者: 王香善 E-mail:xswang@xznu.edu.cn
基金资助:
国家自然科学基金(20802061);江苏省高校自然科学基金资助项目(08KJD150019)

A Clean Synthesis of 1,4-Diarylquinoline-2,5-dione Derivatives in Aqueous Media

Zhang, Meimei^a Li, Qing^b Wu, Jianrong^b Wang, Xiangshan^*,a,b

(^a Key Laboratory of Biotechnology on Medical Plant of Jiangsu Province, Xuzhou Normal University, Xuzhou 221116) (^b School of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116)

Received:2009-02-22 Revised:2009-05-21 Published:2009-06-26

Abstract

A series of 7,7-dimethyl-1,4-diaryl-1,2,3,4,5,6,7,8-octahydroquinoline-2,5-dione derivatives were synthesized in high yields by a three-component reaction of 3-arylamino-5,5-dimethylcyclohex-2- enones, aromatic aldehydes and Meldrum’s acid catalyzed by triethylbenzylammmonium chloride (TEBAC) at reflux in aqueous media. This method had several advantages of neutral reaction conditions, high yields, simple work-up and environmental benignity.

Key words: quinoline, water, TEBAC, synthesis

Cite this article

ZHANG Mei-Mei, LI Qiang, TUN Jian-Rong, WANG Xiang-Shan. A Clean Synthesis of 1,4-Diarylquinoline-2,5-dione Derivatives in Aqueous Media[J]. Chin. J. Org. Chem., 2009, 29(11): 1811-1815.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[2]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[3]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[4]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[7]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[8]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[9]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[10]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[11]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[12]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[13]	Yang Li, Jinding Yuan, Di Zhao. Deep Eutectic Solvent of 1,3-Dimethylurea/L-(+)-Tartaric Acid for the Green Synthesis of (E)-2-Styrylquinoline-3-carboxylic Acid Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3268-3276.
[14]	Dandan Sui, Nannan Cen, Ruoqu Gong, Yang Chen, Wenbo Chen. Supporting-Electrolyte-Free Electrochemical Synthesis of Trifluoromethylated Oxindoles in Continuous Flow [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3239-3245.
[15]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.

水介质中1,4-二芳基喹啉-2,5-二酮衍生物的绿色合成

A Clean Synthesis of 1,4-Diarylquinoline-2,5-dione Derivatives in Aqueous Media

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments