2-氨基-4-羰基噻吩的Knoevenagel反应  

Knoevenagel Reaction of 2-Aminothiophen-4-one

作　　者：王锋[1] 李稳宏[1] 李冬[1] 延绥红[1] 徐抗震[1] 孙晓红[1,2] 

机构地区：[1]西北大学化工学院,西安710069 [2]西北大学化学研究所,西安710069

出　　处：《高等学校化学学报》2011年第4期903-907,共5页Chemical Journal of Chinese Universities

摘　　要：在碳酸钾等无机碱的存在下,异硫氰酸酯和4-氯乙酰乙酸乙酯反应生成2-氨基-4-羰基-4,5-二氢噻吩-3-甲酸乙酯,该产物可与醛进一步发生典型的Knoevenagel反应.通过与一系列醛的合成反应,对该噻吩化合物的Knoevenagel反应的位点选择性进行了研究.同时,运用Gaussian 03程序对2-氨基-4-羰基-4,5-二氢噻吩-3-甲酸乙酯进行了几何全优化和相应的电荷、轨道能量分析,从理论上进一步解释了该化合物的反应活性位点,获得了与合成反应一致的结果.Derivatives of thiophene as new molecule activators of RNase L were found.In this work,ethyl 4,5-dihydro-4-oxo-2-（pyridin-3-ylamino） thiophene-3-carboxylate was successfully synthesized from isothiocya-nate in the presence of sodium carbonate.The thiophene shows typical reactions of aldehydes.Through a large number of synthesis,ethyl 4,5-dihydro-4-oxo-2-（pyridin-3-ylamino） thiophene-3-carboxylate and 5-（pyridin-3-ylamino） thiophen-3（2H）-one show different reaction site with aldehydes.Their structures were confirmedby NMR,ESI-MS and elemental analysis.The oretical investigation was carried out by the use of Gaussian 03 program.The atomic charges and natural bond orbital analyses have been discussed.The result of experimentsaccords with the conclusion drawn by frontier molecular orbital theory.

关 键 词：2-氨基-4-羰基噻吩 理论计算 KNOEVENAGEL反应 

分 类 号：O621.25[理学—有机化学]