5-thioxo-1,5,7,8,9,10-hexahydro[1,2,4]triazolo[3,4-a]isoquinoline-6-carbonitrile | 1269792-65-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并吡啶类
• 英文名称: 5-thioxo-1,5,7,8,9,10-hexahydro[1,2,4]triazolo[3,4-a]isoquinoline-6-carbonitrile
• 英文别名: 5-thioxo-7,8,9,10-tetrahydro-1H-[1,2,4]triazolo[3,4-a]isoquinoline-6-carbonitrile；5-sulfanylidene-7,8,9,10-tetrahydro-1H-[1,2,4]triazolo[3,4-a]isoquinoline-6-carbonitrile
• CAS: 1269792-65-5
• 化学式: C₁₁H₁₀N₄S
• 分子量: 230.293
• InChiKey: CKVBJBVMXJZCDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  83.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-thioxo-1,5,7,8,9,10-hexahydro[1,2,4]triazolo[3,4-a]isoquinoline-6-carbonitrile 在 sodium ethanolate 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 0.42h， 生成 ethyl 7-amino-8,9,10,11-tetrahydrothieno[2,3-c][1,2,4]triazolo[3,4-a]isoquinolin-6-carboxylate
  参考文献：
  名称：

  Synthesis and biological activity of pyrazolothienotetrahydroisoquinoline and [1,2,4]triazolo[3,4-a]thienotetrahydroisoquinoline derivatives

  摘要：

  1-Hydrazino-3-thioxo-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile (3) was subjected to react with bifunctional compounds namely: acetylacetone, ethyl cyanoacetate, ethyl benzoylactate, diethylmalonate and ethyl acetoacetate to produce pyrazololthienotetrahydroisoquinoline derivatives 6-11. Also, heating of compound (3) with formic acid afforded triazolothienotetrahydroisoquinoline compound 5 which reacted with a-halogenated compounds to afford compounds 13a-e. Compound 13c when heated with triethylorthoformate afforded triazolo derivative 14. Also, compound 6 was used for synthesizing compounds 18-20. Representative compounds of the synthesized triazolo and pyrazolothienotetrahydroisoquinoline products were tested and evaluated as antimicrobial agents. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.036
• 作为产物：
  描述：

  2,3,5,6,7,8-六氢-1-吗啉-4-基-3-硫代-异喹啉-4-甲腈 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 5-thioxo-1,5,7,8,9,10-hexahydro[1,2,4]triazolo[3,4-a]isoquinoline-6-carbonitrile
  参考文献：
  名称：

  Synthesis and biological activity of pyrazolothienotetrahydroisoquinoline and [1,2,4]triazolo[3,4-a]thienotetrahydroisoquinoline derivatives

  摘要：

  1-Hydrazino-3-thioxo-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile (3) was subjected to react with bifunctional compounds namely: acetylacetone, ethyl cyanoacetate, ethyl benzoylactate, diethylmalonate and ethyl acetoacetate to produce pyrazololthienotetrahydroisoquinoline derivatives 6-11. Also, heating of compound (3) with formic acid afforded triazolothienotetrahydroisoquinoline compound 5 which reacted with a-halogenated compounds to afford compounds 13a-e. Compound 13c when heated with triethylorthoformate afforded triazolo derivative 14. Also, compound 6 was used for synthesizing compounds 18-20. Representative compounds of the synthesized triazolo and pyrazolothienotetrahydroisoquinoline products were tested and evaluated as antimicrobial agents. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.036

文献信息

• Synthesis of tetracyclic thienotriazolopyridines based on hydrazine derivatives of fused pyridinethiones
  作者：E. G. Paronikyan、Sh. Sh. Dashyan、A. S. Harutyunyan、S. S. Mamyan、E. S. Safaryan

  DOI：10.1007/s11172-022-3503-5

  日期：2022.5

  method for the synthesis of hydrazine derivatives of fused pyridinethiones based on alicyclic and heterocyclic ketones has been developed. Successive heterocyclization of these hydrazine derivatives was carried out in order to obtain new derivatives of tricyclic triazolo[4,3-a]pyridines, tetracyclic thieno[3,2-e][1,2,4]triazolo[4,3-a]pyridines, as well as a new heterocyclic system of thieno[2,3-c][1,2

  开发了一种基于脂环酮和杂环酮的稠合吡啶硫酮肼衍生物的合成方法。对这些肼衍生物进行连续杂环化以获得三环三唑并[4,3- a ]吡啶、四环噻吩并[3,2 -e ][1,2,4]三唑并[ 4,3- a ]的新衍生物]吡啶，以及噻吩并[2,3 - c ][1,2,4]三唑并[3,4- a ]-2,7-萘啶的新杂环体系。
• Synthesis and biological activity of pyrazolothienotetrahydroisoquinoline and [1,2,4]triazolo[3,4-a]thienotetrahydroisoquinoline derivatives
  作者：Adel M. Kamal、Shaban M. Radwan、Remon M. Zaki

  DOI：10.1016/j.ejmech.2010.11.036

  日期：2011.2

  1-Hydrazino-3-thioxo-5,6,7,8-tetrahydroisoquinoline-4-carbonitrile (3) was subjected to react with bifunctional compounds namely: acetylacetone, ethyl cyanoacetate, ethyl benzoylactate, diethylmalonate and ethyl acetoacetate to produce pyrazololthienotetrahydroisoquinoline derivatives 6-11. Also, heating of compound (3) with formic acid afforded triazolothienotetrahydroisoquinoline compound 5 which reacted with a-halogenated compounds to afford compounds 13a-e. Compound 13c when heated with triethylorthoformate afforded triazolo derivative 14. Also, compound 6 was used for synthesizing compounds 18-20. Representative compounds of the synthesized triazolo and pyrazolothienotetrahydroisoquinoline products were tested and evaluated as antimicrobial agents. (C) 2010 Elsevier Masson SAS. All rights reserved.