Synthesis of 4-Hydroxy-6-methyl-[(1-phenylimino)ethyl]-2H-pyran-2- one Derivatives Catalyzed by Ionic Liquid [BMIM-HSO3]HSO4 under Ultrasound

doi:10.6023/cjoc201204020

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2193-2197.DOI: 10.6023/cjoc201204020 Previous Articles Next Articles

Notes

超声波辐射下离子液体催化合成4-羟基-6-甲基-[1-(苯基亚氨基)乙基]-2H-吡喃-2-酮衍生物

李大庆, 臧洪俊, 吴长春, 卢波, 程博闻

天津工业大学环境与化学工程学院天津改性与功能纤维重点实验室天津 300387

收稿日期:2012-04-18 修回日期:2012-06-19 发布日期:2012-07-02
通讯作者: 臧洪俊 E-mail:chemhong@126.com
基金资助:
天津市自然科学基金(No. 11JCZDJC21300)资助项目.

Synthesis of 4-Hydroxy-6-methyl-[(1-phenylimino)ethyl]-2H-pyran-2- one Derivatives Catalyzed by Ionic Liquid [BMIM-HSO₃]HSO₄ under Ultrasound

Li Daqing, Zang Hongjun, Wu Changchun, Lu Bo, Cheng Bowen

State Key Laboratory of Hollow Fiber Membrane Material and Processes, Department of Environmental and Chemistry Engineering, Tianjin Polytechnic University, Tianjin 300387

Received:2012-04-18 Revised:2012-06-19 Published:2012-07-02
Supported by:
Project supported by the Natural Science Foundation of Tianjin City (No. 11JCZDJC21300).

4-Hydroxy-6-methyl-[(1-phenylimino)ethyl)]-2H-pyran-2-one derivatives have been synthesized via the reaction of dehydroacetic acid and amine in the presence of the ionic liquid [BMIM-HSO₃]HSO₄ under ultrasonic irradiation. The effect of catalyst, catalyst amount, reaction temperature and solvent on the yield was investigated. The optimum reaction condition was determined and the possible mechanism was proposed. This method has some distinct advantages such as short reaction time, high yields, environmental friendliness and mild reaction conditions. Moreover, the ionic liquid could be recovered conveniently and reused.

Key words: ionic liquid, ultrasound, dehydroacetic acid, amine

Cite this article

Li Daqing, Zang Hongjun, Wu Changchun, Lu Bo, Cheng Bowen. Synthesis of 4-Hydroxy-6-methyl-[(1-phenylimino)ethyl]-2H-pyran-2- one Derivatives Catalyzed by Ionic Liquid [BMIM-HSO₃]HSO₄ under Ultrasound[J]. Chin. J. Org. Chem., 2012, 32(11): 2193-2197.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Jian Zhang, Wanjie Liang, Yi Yang, Fachao Yan, Hui Liu. Regiocontrollable Difunctionalization of N-Allenamines [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 335-348.
[2]	Yong Zhang, Zhigao Tian, Lin Huang, Qiufei Hou, Honghong Fan, Wanqiang Wang. Application of α-Cyanohydrin Methanesulfonates for the Synthesis of α-Aminonitriles [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 561-572.
[3]	Weizhong Ding, Bingwen Zhang, Yanqing Xue, Yuqi Lin, Zhijun Tang, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. A New Polyketide from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3319-3322.
[4]	Min Xi, Chao Duan, Jie Chi, Tian Fu, Xiaolong Su, Hongshe Wang. An Efficient and Rapid Synthesis of α-Aminonitriles via Strecker Reaction Catalyzed by Humic Acid [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3312-3318.
[5]	Xiangping Chen, Chenxiang Meng, Mengna Li, Shangmin Chu, Xinxin Zhu, Kai Xu, Lantao Liu, Tao Wang, Fenghua Zhang, Fei Li. Fe-Catalyzed Synthesis of Sulfide-Based Aromatic Primary Amines in Water Promoted by Sodium-Ascorbate [J]. Chinese Journal of Organic Chemistry, 2023, 43(8): 2800-2807.
[6]	Zeren Sun, Bingxin Zhai, Guangchao He, Hui Shen, Linya Chen, Shan Zhang, Yi Zou, Qihua Zhu, Yungen Xu. Synthesis and Anti-inflammatory Evaluation of Novel 1,2,3-Triazole Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2143-2155.
[7]	Yiwen Quan, Xinhui Jiang, Wenjun Li, Jian Wang. Access to α-Vinyl β-Alkynyl Enals via an Organocatalytic Deconjugation-Aldol Condensation Sequence [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2120-2125.
[8]	Rongbin Cai, Bing Li, Qi Zhou, Longyi Zhu, Jun Luo. Synthesis of 4,8,9,10-Tetrafunctionalized 2-Azaadamantanes and Their 2-Azaprotoadamantane Skeleton Isomers [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2217-2225.
[9]	Shengjie Jiang, Yang Wang, Xin Xu. Rare-Earth Metal Complexes-Catalyzed Dehydropolymerization of Methylamine-Boranes [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1786-1791.
[10]	Maocai Xu, Jiazhuang Tian, Yanhua Yang, Gaozhang Gou, Fumin Li, Lin Shao, Kexin Chi. Reversible Mechanofluorochromic and Data Security Protection of a Triphenylamine-Based Difluoroboron Luminescent Compound [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1824-1831.
[11]	Yuyuan Liu, Yaqin Lei, Wen Yang, Wanxiang Zhao. Cobalt-Catalyzed Remote Hydroboration of Enamines [J]. Chinese Journal of Organic Chemistry, 2023, 43(5): 1761-1771.
[12]	Xuzheng Zhang, Fengli Yu, Bing Yuan, Congxia Xie, Shitao Yu. Phase Transfer Catalytic Oxidation of Cyclopentene to Glutaraldehyde by Vanadium Molybdenum Heteropolyacid Salts [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1444-1451.
[13]	Wei Wang, Zheyu Zhang, Xue Zhang, Haifeng Yu, Hui Luo, Dongyue Huo, Yupeng Xu, Xiaobo Zhao. Synthesis of Polysubstituted 2,3-Dihydropyridin-4(1H)-one in Water [J]. Chinese Journal of Organic Chemistry, 2023, 43(2): 742-750.
[14]	Qianmin Li, Manman Wang, Wenquan Yu, Junbiao Chang. Synthesis of β-Nitroamines and α-Aminonitriles by I₂-Mediated Oxidative C—C Bond Formation [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 3966-3976.
[15]	Bingwen Zhang, Yuqi Lin, Yanqing Xue, Jing Wang, Wenchao Yang, Xiaofeng Wang, Wen Liu. Study on Secondary Metabolites from Fusarium graminearum [J]. Chinese Journal of Organic Chemistry, 2023, 43(11): 4003-4007.

超声波辐射下离子液体催化合成4-羟基-6-甲基-[1-(苯基亚氨基)乙基]-2H-吡喃-2-酮衍生物

Synthesis of 4-Hydroxy-6-methyl-[(1-phenylimino)ethyl]-2H-pyran-2- one Derivatives Catalyzed by Ionic Liquid [BMIM-HSO₃]HSO₄ under Ultrasound

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments