高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 144.

• Organic Synthesis Chemistry • 上一篇    下一篇

Synthesis of 6-aryl-3-cinchophenyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles

Peng-Fei XU, Lin-Mei ZHANG, Xin-Ping HUI, Zi-Yi ZHANG   

  1. National Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000
  • 出版日期:1998-12-31 发布日期:1998-12-31
  • 通讯作者: Peng-Fei XU

Synthesis of 6-aryl-3-cinchophenyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles

Peng-Fei XU, Lin-Mei ZHANG, Xin-Ping HUI, Zi-Yi ZHANG   

  1. National Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou 730000
  • Online:1998-12-31 Published:1998-12-31
  • Contact: Peng-Fei XU

摘要: In recent years, fused heterocycles have been found to possess many unique properties in synthesis and pharmacology. Especially, 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles derivatives have been attracting much attention of chemists and pharmacologists because of their broad-spectrum biological activities such as antibacterial1, hypotensive and CNS depressant2 activities. We have prepared some 3,6-substituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and found that these compounds exhibited antimacrobial, insecticidal and promote plant growth.3-5 Cinchophen had been used widely as medicine in clinic,but has been obsolete in recent years due to its by-effect. In order to seek for other uses of cinchophen, as a continuation of our preceeding studies, we used cinchophen as the starting material to synthesize ten new 6-aryl-3-cinchophenyl-l,2,4-triazolo[3,4-b]-l,3,4-thiadiazoles 5a-j. Compound 1 was prepared by the reaction of cinchophen and ethanol in the presence of sulfuric acid. 1 then reacted with hydrazine hydrate in absolute ethanol to give 2 which yielded 3 on treatment with CS2 and KOH. On refluxing of 3 with excess hydrazine hydrate, 4 was obtained. 4 reacted with various substituted benzoic acids in the presence of POCl3 to afifort 5a-j.

Abstract: In recent years, fused heterocycles have been found to possess many unique properties in synthesis and pharmacology. Especially, 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles derivatives have been attracting much attention of chemists and pharmacologists because of their broad-spectrum biological activities such as antibacterial1, hypotensive and CNS depressant2 activities. We have prepared some 3,6-substituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazoles and found that these compounds exhibited antimacrobial, insecticidal and promote plant growth.3-5 Cinchophen had been used widely as medicine in clinic,but has been obsolete in recent years due to its by-effect. In order to seek for other uses of cinchophen, as a continuation of our preceeding studies, we used cinchophen as the starting material to synthesize ten new 6-aryl-3-cinchophenyl-l,2,4-triazolo[3,4-b]-l,3,4-thiadiazoles 5a-j. Compound 1 was prepared by the reaction of cinchophen and ethanol in the presence of sulfuric acid. 1 then reacted with hydrazine hydrate in absolute ethanol to give 2 which yielded 3 on treatment with CS2 and KOH. On refluxing of 3 with excess hydrazine hydrate, 4 was obtained. 4 reacted with various substituted benzoic acids in the presence of POCl3 to afifort 5a-j.

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