超声辅助或无溶剂Claisen-Schmidt反应合成含胡椒环的吲哚查尔酮(英文)  

A facile synthesis of 1,3-benzodioxole-bearing indole-based chalcone via ultrasound-assisted or solvent-free Claisen-Schmidt condensation reaction

作　　者：李阳[1] 

机构地区：[1]渤海大学超精细化学品研究所,辽宁锦州121000

出　　处：《化学研究与应用》2014年第1期108-112,共5页Chemical Research and Application

摘　　要：3-乙酰基-2-氯-1-(4-氯苄基)吲哚与胡椒醛通过超声辅助或无溶剂的Claisen-Schmidt缩合反应首次合成含胡椒环的吲哚查尔酮,即(E)-3-(5-胡椒基)-1-(2-氯-1-(4-氯苄基)-1H-3-吲哚查尔酮(3)。超声辅助的合成方法使用5%KOH作为催化剂,1,4-二氧六环作为溶剂,以78%的收率得到产品3。另外,这一ClaisenSchmidt反应也可以在无溶剂研磨条件下进行,同样也以类似的收率获得产品3(75%)。这两种方法具有操作简便、反应条件温和、收率高等优点。A structurally novel 1,3-benzodioxole-bearing indole-based chalcone,namely（E）-3-（benzo[d][1,3]dioxol-5-yl）-1-（2-chloro-1-（4-chlorobenzyl）-1H-indol-3-yl） prop-2-en-1-one（3） was synthesized,involving the ultrasound-assisted or solvent-free Claisen-Schmidt condensation reaction of 3-acetyl-2-chloro-1-（4-chlorobenzyl） indole and piperonaldehyde. The ultrasound-assisted Claisen-Schmidt condensation reaction was carried out using 1,4-dioxane as solvent and KOH as catalyst at room temperature to give the product 3 in 78%yield. Alternatively,the reaction could also be conducted under solvent-free condition by physical grinding in a mortar and pestle to obtain 3 in comparable yield of 75%. The two procedures offered easy access to 1,3-benzodioxole-bearing indole-based chalcone in short reaction time and good yield under mild conditions.

关 键 词：胡椒环 吲哚 查尔酮 超声辅助 无溶剂 Claisen-Schmidt缩合 

分 类 号：O625[理学—有机化学]