3-芳基-5-巯基-1.2.4-三唑的亲核取代反应研究

Study on the Nucleophilic Substitution of 3 - Aryl - 5 - Mercapto -1,2,4- Triazole

以3-芳基-5-巯基-1.2.4-三唑为原料合成了20个3-芳基-1.2.4-三唑-5-巯基乙酸乙酯(2a～e)、3-芳基-1.2.4-三唑-5-巯基乙酸(3a～e)、3-劳基-5,6-二氢噻唑并[2,3-c]均三唑(5a～e)和3-芳基-6,7-二氢均三唑并[3,4-b][1,3]噻嗪(6a～e)。研究了3a～e在微波辐射下的环化反应,合成了5个3-芳基-5-氧代-6H-噻唑[2.3-c]均三唑(4a～e)。产物经元素分析、红外、核磁共振以及质谱方法确定了结构。初步研究了代表化合物的生物活性。

Ten 3 - aryl - 1.2.4 - triazol - 5 - alkylsulfides were prepared by the reaction of 3 -aryl - 5 - mercapto -1.2.4 - triazoles with chloroacetic acid and ethyl bromoacetate in the presence of a base. Five 3 - arylthiazolo[2,3 - c] - s - triazol - 5(6H) - ones were synthesized by cyclization under the condition of microwave irradiation. Ten 3 - aryl - 6,7 - dihydro - s - triazolo[3,4 - b] [ 1, 3] thiazine and 3 - aryl - 5,6 - dihydrothiazolo [2,3 - c]- s - riazoles were synthesized by nucleophilicsubstitution of 3 - aryl - 5 - mercapto -1,2,4 - triazoles with dihalohydrocarbon 1,2 -dichloroethane and 1,3 - dibromopropane in isopropanol and alkaline media. The structure of all compounds were characterized by elemental analysis, IR, 1H NMR and MS. The compounds have been evaluated for their antibacterial activity against E. Coli;B. Sub;S. Aur. Compound 3a showed anticancer activity.