高等学校化学学报

高等学校化学学报 ›› 1998, Vol. 19 ›› Issue (S1): 308.

• Organic Synthesis Chemistry • 上一篇    下一篇

Syntheses of Chiral Fused Heterocyclic Compounds Containing l,2,4-Triazole Ring

Wang Zhongyi1,2, You Lingfeng1, You Tianpa1, Shi Haijian2, Shi Haoxin2   

  1. 1. Department of Chemistry, University of Science and Technology of China, Hefei 230026;
    2. Department of Chemistry, Anhui Normal University, Wuhu 241000
  • 出版日期:1998-12-31 发布日期:1998-12-31
  • 基金资助:
    This work was supported by the National Natural Science Foundation of China and the Natural Science Foundation of Anhui Province

Syntheses of Chiral Fused Heterocyclic Compounds Containing l,2,4-Triazole Ring

Wang Zhongyi1,2, You Lingfeng1, You Tianpa1, Shi Haijian2, Shi Haoxin2   

  1. 1. Department of Chemistry, University of Science and Technology of China, Hefei 230026;
    2. Department of Chemistry, Anhui Normal University, Wuhu 241000
  • Online:1998-12-31 Published:1998-12-31
  • Supported by:
    This work was supported by the National Natural Science Foundation of China and the Natural Science Foundation of Anhui Province

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摘要： The chemistry of life is based considerably on chirality. Consequently, stereospecificity has to be regarded as an especially important characteristic of biological systems. The influence of stereospecificity of the biological activities of enzyme inhibitors or compounds binding to receptor is a well known fact in the field of drug action[1]. s-Triazoles and l,3,4-thiadiazoles are reported to exhibit broad spectrum of biological and pesticidal activities[2-3].In recent years, bridge head nitrogen heterocycles have received much attention as anthelmintic agents, however, it is not observed that the syntheses of chiral fused heterocyclic compounds containing s-triazoles and l,3,4-thiadiazoles. In order to study the relationship between stereochemistry and the performance of fungicides, we have synthesized a series of (s)-1,2-di(3-aryl-s-triazolo[3,4-b][1,3,4] thiadiazolo-6-yl) ethylamine and (s)-1-(3-aryl-s-triazolo[3,4-b][l,3,4] thiadiazolo-6-yl) ethylamine by the condensation of 3-aryl-4-amino-5-mercapto-1,2,4-triazoles with L-aspartic acid and L-alanine in the presence of phosphorusoxychloride.

Abstract: The chemistry of life is based considerably on chirality. Consequently, stereospecificity has to be regarded as an especially important characteristic of biological systems. The influence of stereospecificity of the biological activities of enzyme inhibitors or compounds binding to receptor is a well known fact in the field of drug action[1]. s-Triazoles and l,3,4-thiadiazoles are reported to exhibit broad spectrum of biological and pesticidal activities[2-3].In recent years, bridge head nitrogen heterocycles have received much attention as anthelmintic agents, however, it is not observed that the syntheses of chiral fused heterocyclic compounds containing s-triazoles and l,3,4-thiadiazoles. In order to study the relationship between stereochemistry and the performance of fungicides, we have synthesized a series of (s)-1,2-di(3-aryl-s-triazolo[3,4-b][1,3,4] thiadiazolo-6-yl) ethylamine and (s)-1-(3-aryl-s-triazolo[3,4-b][l,3,4] thiadiazolo-6-yl) ethylamine by the condensation of 3-aryl-4-amino-5-mercapto-1,2,4-triazoles with L-aspartic acid and L-alanine in the presence of phosphorusoxychloride.

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