SIOC English
有机化学
高级检索

有机化学 ›› 1997, Vol. 17 ›› Issue (6): 535-541. 上一篇    下一篇

研究论文

3-芳基-5-巯基-1,2,4-三唑的亲核取代反应研究

王忠义;尤田耙;史海健;史好新   

  1. 中国科学技术大学化学系;安徽师范大学化学系
  • 发布日期:1997-12-25

Study on the nucleophilic substitution of 3-aryl-5-mercapto- 1,2,4-triazole

WANG ZHONGYI;YOU TIANPA;SHI HAIJIAN;SHI HAOXIN   

  • Published:1997-12-25

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-芳基-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。

关键词: 亲核反应, 噻嗪 P, 乙酸 P, 噻唑 P, 三唑 P, 有机合成, 环化, 生物活性, 巯基化合物, 取代反应

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.

Key words: NUCLEOPHILIC REACTION, ACETIC ACID P, THIAZINE P, BIOLOGICAL ACTIVITY, PYRRODIAZOLE P, CYCLIZATION, ORGANIC SYNTHESIS, MERCAPTO COMPOUNDS, SUBSTITUTION REACTION, THIAZOLE P

中图分类号: