聚乙二醇中合成对甲苯磺酰腙衍生物的研究
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摘要
探讨了对甲苯磺酰肼与某种含苯环的酮醛类化合物,以无毒且可回收利用的聚乙二醇取代污染性较大的甲醇为溶剂发生反应,用于合成对甲苯磺酰腙衍生物,以及在不同温度时该反应的反应情况和绿色溶剂的重复使用效果。研究结果表明:该反应在70℃下在聚乙二醇中进行,合成对甲苯磺酰腙衍生物,与用甲醇做溶剂相比,在反应时间上并无太大差异,且由于聚乙二醇的无毒以及可回收性,使得该反应更加绿色环保且节约成本。此外,在70℃的反应温度下,该反应显然更高效,且溶剂重复使用4次效果变化不大。
The reaction between p-toluenesulfonyl hydrazide and a certain benzene ring-containing ketone aldehyde compound in non-toxic and recyclable polyethylene glycol solvent to synthesize p-toluenesulfonylhydrazine derivatives was investigated, as well as the effect of temperature and solvent reuse times on the reaction. The results showed that p-toluenesulfonylhydrazine derivatives were synthesized in polyethylene glycol at 70 ℃; Compared with the reaction with methanol as solvent, there is not much different in the reaction time, and the non-toxic and recyclable proterties of polyethylene glycol made the reaction more environmentally friendly and the cost was reduced. Further,at a reaction temperature of 70 ℃, the reaction was more efficient, and the effect of solvent in reusing for 4 times did not change much.
The reaction between p-toluenesulfonyl hydrazide and a certain benzene ring-containing ketone aldehyde compound in non-toxic and recyclable polyethylene glycol solvent to synthesize p-toluenesulfonylhydrazine derivatives was investigated, as well as the effect of temperature and solvent reuse times on the reaction. The results showed that p-toluenesulfonylhydrazine derivatives were synthesized in polyethylene glycol at 70 ℃; Compared with the reaction with methanol as solvent, there is not much different in the reaction time, and the non-toxic and recyclable proterties of polyethylene glycol made the reaction more environmentally friendly and the cost was reduced. Further,at a reaction temperature of 70 ℃, the reaction was more efficient, and the effect of solvent in reusing for 4 times did not change much.
引文
[1]ROLLASS,KUCUKGUZEL SG.Biological Activities of Hydrazone Derivatives[J].Molecules,2007,12:1910-1939.
[2]POLSHETTIWAR V,VARMA R S.Polystyrene sulfonic acid-catalyzed greener synthesis of hydrazones in aqueous medium using microwaves[J].Tetrahedron Lett,2007,48:5649-5652.
[3]许恺,沈冲,单尚.对甲苯磺酰腙的偶联反应研究进展[J].有机化学,2015,35,294-308.
[4]辛炳伟,PEG参与的Suzuki反应研究进展[J].榆林学院学报,2008,18(2):61-64.
[5]钟克利,杜晓,励建荣.聚乙二醇改性壳聚糖作为小分子药物载体的研究进展[J].化学通报,2014(02):131-136.
[6]周海峰,范清华,何艳梅,等.液态聚乙二醇作为绿色反应介质在有机反应中的应用[J].化学进展,2007,19(10):1517-1528.
[7]MAJID.V,MOHAMMAD.M.H.Polyethylene Glycol(PEG)as a Green Solvent for Carbon-carbon Bond Formation Reactions[J].J.Mol.Liq.,2015,207(28):73-79
[8]王喜存,叶鹤琳,权正军,等.芳基亚甲基麦氏酸在PEG-400中的绿色合成[J].西北师范大学学报(自然科学版),2009(3):79-82.
[9]秦瑞香,王金波,熊伟,等.聚乙二醇400-水介质中水溶性钌膦二胺催化苄叉丙酮的不对称加氢反应[J].催化学报,2012(7):1146-1153.
[10]Dhanaji V.Jawale,Dinesh.L.Lingampalle,Umesh R.Pratap,Ramrao A.Mane.One-pot synthesis of 2-aminothiazoles in PEG-400[J].CHINESE CHEM LETT,2012(7):413-415.
[2]POLSHETTIWAR V,VARMA R S.Polystyrene sulfonic acid-catalyzed greener synthesis of hydrazones in aqueous medium using microwaves[J].Tetrahedron Lett,2007,48:5649-5652.
[3]许恺,沈冲,单尚.对甲苯磺酰腙的偶联反应研究进展[J].有机化学,2015,35,294-308.
[4]辛炳伟,PEG参与的Suzuki反应研究进展[J].榆林学院学报,2008,18(2):61-64.
[5]钟克利,杜晓,励建荣.聚乙二醇改性壳聚糖作为小分子药物载体的研究进展[J].化学通报,2014(02):131-136.
[6]周海峰,范清华,何艳梅,等.液态聚乙二醇作为绿色反应介质在有机反应中的应用[J].化学进展,2007,19(10):1517-1528.
[7]MAJID.V,MOHAMMAD.M.H.Polyethylene Glycol(PEG)as a Green Solvent for Carbon-carbon Bond Formation Reactions[J].J.Mol.Liq.,2015,207(28):73-79
[8]王喜存,叶鹤琳,权正军,等.芳基亚甲基麦氏酸在PEG-400中的绿色合成[J].西北师范大学学报(自然科学版),2009(3):79-82.
[9]秦瑞香,王金波,熊伟,等.聚乙二醇400-水介质中水溶性钌膦二胺催化苄叉丙酮的不对称加氢反应[J].催化学报,2012(7):1146-1153.
[10]Dhanaji V.Jawale,Dinesh.L.Lingampalle,Umesh R.Pratap,Ramrao A.Mane.One-pot synthesis of 2-aminothiazoles in PEG-400[J].CHINESE CHEM LETT,2012(7):413-415.