2-[1-(1H-苯并三唑)甲基-]5-芳基-1,3,4-噁二唑化合物的合成与结构表征

Synthesis and structural characterization of 2-[1-(1H-benzotriazole)methyl]-5-aryl-1,3,4-oxadiazoles

首先以苯并三氮唑为原料,在无水K2 CO3 、PEG 60 0和乙腈的作用下,与氯乙酸乙酯反应制得1H -苯并三唑乙酸乙酯,再以无水乙醇为溶剂,于1 0 5～1 1 0℃,与80 %的水合肼反应8h,制得1H 苯并三唑乙酰肼。然后该化合物在以碳酸钠作缚酸剂,温度40℃的条件下分别与苯甲酰氯、4 -氯苯甲酰氯、3 ,4,5 - 三甲氧基苯甲酰氯、4 -硝基苯甲酰氯、4- 甲氧基苯甲酰氯、2- 氯苯甲酰氯和呋喃甲酰氯和反应得到相应的N ,N′- 二酰基肼。最后分别在POCl3 作用下,脱水环化成了2 - [1 -(1H -苯并三唑)甲基]- 5 - 芳基1 ,3 ,4 -噁二唑化合物,通过元素分析,IR ,1HNMR和MS对化合物的结构进行了表征。

1H-benzotrizol-1-acetate(1)was prepared by reaction of 1H-benzotrizol with ethyl chloroacetate in the presence of anhydrous potassium carbonate,PEG-600 and acetonitrile.This compound reacted with hydrazine hydrate(80%)for 8h in the presence of anhydrous ethanol as solvent to give 1H-benzotrizol-1-acetic acid hydrazine(2).In the presence of Na_2CO_3 as acid acceptor at 40℃,2 respectively reacted with benzoyl chloride,4-chlorobenzoyl chloride,3,4,5-trimethoxybenzoyl chloride,4-nitrobenzoyl chloride,4-methoxybenzoyl chloride,2-chlorobenzoyl chloride and 4-furoyl chloride to yield N,N ′-diacylhydrazines( 3a～ 3g).Then 3a～3g respectively cyclodehydrated with POCl_3 to afford 2-[1-(1H-benzotriazole)methyl]-5-aryl-1,3,4-oxadiazoles(4a～4g),and the structures of 4a～4g were confirmed by elemental analyses,IR, 1HNMR ,and MS spectroscopy.