含1,3,4-噁二唑和1,3,4-噻二唑的硫醚类化合物的合成有机化学.pdfVIP

2011 年第 31 卷 有 机 化 学 Vol. 31, 2011 第 6 期, 824～831 Chinese Journal of Organic Chemistry No. 6, 824～831 ·研究论文· 含 1,3,4-噁二唑和 1,3,4-噻二唑的硫醚类化合物的合成 武现丽 朱春风 吕志丹 魏成事 廖新成* (郑州大学化学系 郑州 450052) 摘要 在 KOH 作用下, 芳甲酰肼 1a～1e 与 CS2 环化生成 5-芳基-2-巯基-1,3,4-噁二唑(2a～2e); 将 2a～2e 与氯乙酸乙 酯反应, 生成 2-(5-芳基-1,3,4-噁二唑)硫基乙酸乙 (3a～3e); 3a～3e 肼解得 2-(5-苯基-1,3,4-噁二唑-2-硫基) 乙酰肼(4a～ 4e); 4a～4e 与芳酰基异硫氰酸 5a～5d 反应得到双酰基氨基硫脲衍生物 A1～A19; A1～A19 在 H SO 催化下环合得 2 4 到目标化合物 B1～B19; 目标化合物的结构经IR, 1H NMR, MS, HRMS 确证. 关键词 1,3,4-噁二唑; 1,3,4-噻二唑; 氨基硫脲; 硫醚 Synthesis of Sulfur Ethers Containing 1,3,4-Oxadiazole and 1,3,4-Thiadiazole Wu, Xianli Zhu, Chunfeng Lü, Zhidan Wei, Chengshi Liao, Xincheng* (Department of Chemistry, Zhengzhou University, Zhengzhou 450052) Abstract 5-Aryl-2-mercapto-1,3,4-oxadiazoles (2a～2e) have been obtained by the reaction of arylcar- boxylic acid hydrazides 1a～1e with carbon disulfide in the presence of potassium hydroxide. Then the re- action of compounds 2a～2e with ethyl chloroacetate produced 2-(5-aryl-1,3,4-oxadiazol)thio esters (3a～ 3e). The treatment of compounds 3a～3e with hydrazine hydrate resulted in the formation of acide hy- drazides 4a～4e. The biacyl thiosemicarbazide derivatives A1～A19 were synthesized by the reaction of corresponding compounds 4a～4e with aroyl isothiocyanates 5a～5d. The target co