磷酸二苯酯催化的2-吲哚甲烷胺衍生物的合成  

Synthesis of 2-indolyl methanamine derivatives catalyzed by diphenyl phosphate

作　　者：张首琪 曹阳[1,2] ZHANG Shouqi;CAO Yang(School of Pharmaceutical Science and Technology,Tianjin University,Tianjin 300072,China;Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening,Jiangsu Ocean University,Lianyungang 222005,Jiangsu,China)

机构地区：[1]天津大学药物科学与技术学院,天津300072 [2]江苏海洋大学江苏省海洋药物筛选重点实验室,连云港江苏222005

出　　处：《精细化工》2021年第9期1940-1944,共5页Fine Chemicals

基　　金：江苏海洋大学人才引进科研基金。

摘　　要：以磷酸二苯酯为催化剂,3-甲基吲哚类化合物与亚胺通过Friedel-Crafts加成反应一步合成了具有广泛药理活性的2-吲哚基甲烷胺类化合物,对反应条件进行优化。结果表明,当n(3-甲基吲哚类化合物)∶n(亚胺化合物)∶n(磷酸二苯酯)=1.0∶2.0∶0.1,其中,当以0.0025 mmol磷酸二苯酯为催化剂,1 mL无水二氯甲烷为溶剂,室温下反应30min时,即可得到高收率2-吲哚基甲烷胺类衍生物(85%~90%)。产物经^(1)HNMR、^(13)CNMR和HRMS进行了结构确定,并推测了反应机理。Friedel-Crafts reaction of 3-methylindoles and imines catalyzed by diphenyl phosphate was used to synthesize 2-indolyl methanamines with a wide range of pharmacological activities in one step. The reaction conditions were optimized and the optimal reaction conditions were obtained as follows: n(3-methylindoles)∶n(imines)∶n(diphenyl phosphate) = 1.0∶2.0∶0.1, 0.0025 mmol diphenyl phosphate as catelyst, 1 mL anhydrous dichloromethane as solvent, room temperature for 30 min. Under the above-mentioned conditions, 2-indolyl methanamine derivatives were obtained in good yields(85%~90%). The structures of the products were confirmed by ^(1)HNMR, ^(13)CNMR and HRMS. The reaction mechanism was speculated.

关 键 词：3-甲基吲哚 亚胺 磷酸二苯酯 2-吲哚基甲烷胺 FRIEDEL-CRAFTS反应 精细化工中间体 

分 类 号：O621.3[理学—有机化学] O626[理学—化学]