超声-微波辅助合成2-吡啶基噁唑啉化合物  

Synthesis of 2-pyridyl Oxazoline Compounds under Ultrasonic-Microwave Irradiation

作　　者：武春阳[1] 顾承志[1] 代斌[1] 

机构地区：[1]石河子大学化学化工学院/化工绿色过程重点实验室/省部共建国家重点实验室培育基地,石河子832003

出　　处：《石河子大学学报（自然科学版）》2012年第4期498-502,共5页Journal of Shihezi University(Natural Science)

基　　金：国家"十五"攻关"创新药物与中药现代化"新药博士基金项目(2003AA2Q3516)

摘　　要：以吡啶甲酸和氨基醇为原料,1-乙基-3-(3-二甲基丙胺)碳二亚胺盐酸盐(EDCI)和1-羟基苯并三氮唑一水物(HOBt.H2O)为缩合剂,得到β-羟基酰胺,产率在95%以上;再用三氯氧磷处理,得到β-氯代酰胺,产率在69%以上;最后在超声-微波辅助条件下,用NaOH的甲醇溶液处理β-氯代酰胺10min,合成2-吡啶基噁唑啉化合物,产率在86%以上。目标化合物的结构经1 H NMR及13 C NMR高分辨质谱确认。考察β-氯代酰胺、氢氧化钠的物质的量比、水和甲醇用量、辐照时间、微波功率以及反应温度对合成2-吡啶基噁唑啉化合物的影响,当氯代酰胺为1.6mmol时,其较优结果分别为1∶40、10和25mL、10min、80W以及50℃。1-ethyl-3-（3-dimethyl-propylamine） carbodiimide hydrochloride and 1-hydroxy-1H-benzotriazole monohydrate were employed in the condensations of picolinate and amino alcohols to afford the corresponding β-hydroxy amide exclusively in high yields.Then synthesis of β-chloro-amide using the acylation of β-hydroxy amide in the presence of phosphoryl trichloride,the yield was over 69%.The target compounds were synthesized in a single step action on β-chloro-amide in sodium hydroxide/water/metha-nol under ultrasonic-microwave irradiation in a good yield.The structure of compounds was charactered by 1HNMR,13CNMR,HRMS.When β-chloro amide was 1.6 mmol,the optimum conditions were as follows：n（β-chloro amide）∶（sodium hydroxide）=1∶40,water 10 mL,methnol 25 mL,irradiation time 10 min,microwave power 80 W,reaction temperature 50 ℃,ultrasonic power 50 W.

关 键 词：氨基醇 吡啶甲酸 2-吡啶基噁唑啉化合物 超声-微波 

分 类 号：O626.24[理学—有机化学] TQ460.31[理学—化学]