2-芳酰氨基-5-苄基-1,3,4-噻二唑的合成及其与苯甲醛反应的研究

Synthesis of 2-Aroylamido-5-benzyl-1,3,4-thiadiazoles and Studies on Their Reactions with Benzaldehyde

1-酰基-4-芳基氨基硫脲类在酸催化下环化为具有广泛生物活性的2-芳氨基-5-芳基-1,3,4-噻二唑类的反应报道甚多,但1,4-二酰基氨基硫脲在相同条件下环化为类似结构衍生物的反应报道很少。为探索其规律,本文研究了1-苯乙酰基-4-芳酰氨基硫脲1a-m在冰醋酸存在下的环化反应,制得2-芳酰氨基-5-苄基-1,3,4-噻二唑2a-m。参考文献还探索了2a-m在EtONa/EtOH体系中与苯甲醛的反应。得到预期产物2-芳酰氨基-5-（1′-苯基-2′-羟基苯乙基）-1,3,4-噻二唑3a-m,经元素分析、IR、1H NMR及MS确认了产物结构。

In this paper, thirteen new 2-aroylamido-5-benzyl-1, 3, 4-thiadiazoles 2a-m were synthesized by cyclization 1-phenylacetyl-4-aroylthiosemicarbazides la-m in ice acetic acid. Thirteen new 2-aroylamido-5-(1'-phenyl-2'-hydroxyphenylethyl)-l,3,4-thiadiazoles 3a-m were obtained by nucle-ophilic addition of benzyl carbanion of 2a-m with benzaldehyde in EtONa-EtOH solution. The structures of compounds 2a_m and those of 3a_ra were confirmed by elementary analysis, IR, 1H NMR, and MS.