1-Methylimidazolium Hydrogen Sulfate： An Efficient Catalyst for the Synthesis of Substituted Pyrroles

doi:10.6023/cjoc201305012

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (11): 2417-2422.DOI: 10.6023/cjoc201305012 Previous Articles Next Articles

Notes

离子液体1-甲基咪唑硫酸氢盐催化合成取代吡咯衍生物

吴长春^a, 臧洪俊^a, 李大庆^a, 於年琴^a, 程博闻^a, 于楷^b

a 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;
b 铁岭港华燃气有限公司铁岭 112002

收稿日期:2013-05-13 修回日期:2013-07-06 发布日期:2013-07-19
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.

1-Methylimidazolium Hydrogen Sulfate： An Efficient Catalyst for the Synthesis of Substituted Pyrroles

Wu Changchun^a, Zang Hongjun^a, Li Daqing^a, Yu Nianqin^a, Cheng Bowen^a, Yu Kai^b

a Department of Environmental and Chemistry Engineering, Tianjin Polytechnic University, Tianjin 300387;
b Ganghua Gas Limited Company, Tieling 112002

Received:2013-05-13 Revised:2013-07-06 Published:2013-07-19
Supported by:
Project supported by the Natural Science Foundation of Tianjin City (No. 11JCZDJC21300).

Using ionic liquid [HMIM]HSO₄ as a eco-friendly catalyst, a variety of N-substituted pyrroles were synthesized by the reaction of 2, 5-hexanedione and primary amines in methanol at reflux. The new compounds were characterized by ¹H NMR, FT-IR, mass spectra and elemental analysis. The influence of different catalysts and catalyst loading were investigated, and the optimal reaction conditions were then obtained. A possible mechanism was also proposed. Furthermore, the recycling experiment of the catalyst was conducted and the green catalytic system can be recycled for several times with no decreases in yields and reaction rates. The present methodology offers several advantages such as mild conditions, short reaction time, excellent yields, and recyclable catalyst.

Key words: pyrroles, ionic liquid, 2,5-hexanedione, amine, eco-friendly catalyst

Cite this article

Wu Changchun, Zang Hongjun, Li Daqing, Yu Nianqin, Cheng Bowen, Yu Kai. 1-Methylimidazolium Hydrogen Sulfate： An Efficient Catalyst for the Synthesis of Substituted Pyrroles[J]. Chin. J. Org. Chem., 2013, 33(11): 2417-2422.

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离子液体1-甲基咪唑硫酸氢盐催化合成取代吡咯衍生物

1-Methylimidazolium Hydrogen Sulfate： An Efficient Catalyst for the Synthesis of Substituted Pyrroles

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