An Efficient and Environmentally Friendly Procedure for Synthesis of Pyridazine Derivatives in Ionic Liquids

doi:10.6023/cjoc201310054

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (5): 968-972.DOI: 10.6023/cjoc201310054 Previous Articles Next Articles

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离子液体中哒嗪衍生物的高效、绿色合成方法研究

陈婷婷, 刘昆, 陈兆祥, 王媛媛, 戴立益

华东师范大学化学系上海 200241

收稿日期:2013-10-31 修回日期:2013-01-08 发布日期:2014-01-10
通讯作者: 王媛媛，戴立益 E-mail:yywang@chem.ecnu.edu.cn;lydai@chem.ecnu.edu.cn
基金资助:
国家自然科学基金（Nos. 21003049，21073064 ）资助项目.

An Efficient and Environmentally Friendly Procedure for Synthesis of Pyridazine Derivatives in Ionic Liquids

Chen Tingting, Liu Kun, Chen Zhaoxiang, Wang Yuanyuan, Dai Liyi

Department of Chemistry, East China Normal University, Shanghai 200241

Received:2013-10-31 Revised:2013-01-08 Published:2014-01-10
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21003049, 21073064).

Imidazolium ionic liquids have been investigated as reaction media in inverse-type Diels-Alder reactions between 1,2,4,5-tetrazine and a series of dienophiles to synthesize pyridazine derivatives for the first time. Comparing to conventional synthetic methods, using easily accessible imidazolium ionic liquids as solvent and catalyst, the reaction time reduced from 13 d to 6 h and product yields increased from 64.0% to 85.5%. The interaction between ionic liquid and reactants in theoretical way was further researched and the most possible catalytic mechanism was proposed. The reaction condition is mild and easy to operate, avoiding using the volatile organic solvents and additional catalysts. Moreover, ionic liquids can be used for more than six times without obvious loss of product yields. Therefore, the current synthetic approach is more in accordance with green chemistry and atom economy requirements.

Key words: pyridazine derivative, 1,2,4,5-tetrazine, dienophile, inverse-type Diels-Alder reaction, imidazolium ionic liquid

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Chen Tingting, Liu Kun, Chen Zhaoxiang, Wang Yuanyuan, Dai Liyi. An Efficient and Environmentally Friendly Procedure for Synthesis of Pyridazine Derivatives in Ionic Liquids[J]. Chin. J. Org. Chem., 2014, 34(5): 968-972.

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离子液体中哒嗪衍生物的高效、绿色合成方法研究

An Efficient and Environmentally Friendly Procedure for Synthesis of Pyridazine Derivatives in Ionic Liquids

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