Synthesis of Sulfur Ethers Containing 1,3,4-Oxadiazole and 1,3,4-Thiadiazole

Chin. J. Org. Chem. ›› 2011, Vol. 31 ›› Issue (06): 824-831. Previous Articles Next Articles

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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)

收稿日期:2010-09-10 修回日期:2011-01-10 发布日期:2011-01-21
通讯作者: 廖新成 E-mail:lxc66@zzu.edu.cn

Synthesis of Sulfur Ethers Containing 1,3,4-Oxadiazole and 1,3,4-Thiadiazole

WU Xian-Li, ZHU Chun-Feng, LV Zhi-Dan, WEI Cheng-Shi, LIAO Xin-Cheng

(Department of Chemistry, Zhengzhou University, Zhengzhou 450052)

Received:2010-09-10 Revised:2011-01-10 Published:2011-01-21
Contact: Xin-Cheng Liao E-mail:lxc66@zzu.edu.cn

5-Aryl-2-mercapto-1,3,4-oxadiazoles (2a～2e) have been obtained by the reaction of arylcarboxylic acid hydrazides 1a～1e with carbon disulfide in the presence of potassium hydroxide. Then the reaction 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 hydrazides 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 compounds B1～B19 were prepared by cyclization of compouds A1～A19 in the presence of CH₃OH/H₂SO₄, and their structures were confirmed by IR, ¹H NMR, MS and HRMS techniques.

Key words: 1,3,4-oxadiazole, 1,3,4-thiadiazole, thiosemicarbazide, sulfur ether

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WU Xian-Li, ZHU Chun-Feng, LV Zhi-Dan, WEI Cheng-Shi, LIAO Xin-Cheng. Synthesis of Sulfur Ethers Containing 1,3,4-Oxadiazole and 1,3,4-Thiadiazole[J]. Chin. J. Org. Chem., 2011, 31(06): 824-831.

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含1,3,4-噁二唑和1,3,4-噻二唑的硫醚类化合物的合成

Synthesis of Sulfur Ethers Containing 1,3,4-Oxadiazole and 1,3,4-Thiadiazole

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