ethyl 1-(4-tolyl)-5-oxo-6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-3-carboxylate | 1177417-16-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 1-(4-tolyl)-5-oxo-6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-3-carboxylate
• 英文别名: ethyl 12-(4-methylphenyl)-16-oxo-8-thia-10,12,13,15-tetrazatetracyclo[7.7.0.02,7.011,15]hexadeca-1(9),2(7),10,13-tetraene-14-carboxylate
• CAS: 1177417-16-1
• 化学式: C₂₁H₂₀N₄O₃S
• 分子量: 408.481
• InChiKey: MBJIBRBNDZSDTG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-疏基-5,6,7,8-四氢-3H-苯并[4,5]噻吩并[2,3-d]嘧啶-4-酮 、 ethyl 2-chloro-(4-tolylhydrazono)acetate 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 ethyl 1-(4-tolyl)-5-oxo-6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-3-carboxylate
  参考文献：
  名称：

  A facile one-pot synthesis of 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones

  摘要：

  The reaction of 2-mercapto-6,7,8,9-tetrahydro3H-benzo[4,5]thieno[2,3- d] pyrimidin-4-one or its 2-methylthio derivative with hydrazonoyl halides, in the presence of triethylamine, yielded 6,7,8,9-tetrahydrobenzo[4,5] thieno [2,3- d]-1,2,4-triazolo[4,5-a] pyrimidin-5-ones. The structure of the latter compounds was further confirmed by reaction of 2-mercapto-6,7,8,9-tetrahydro-3H- benzo[4,5] thieno[2,3- d] pyrimidin-4-one with the appropriate active chloromethylenes followed by coupling of the products with benzenediazonium chloride to afford the non-isolable azocoupling products which converted, in situ, to 6,7,8, 9-tetrahydrobenzo[4,5] thieno[2,3- d]-1,2,4-triazolo[4,5- a] pyrimidin- 5- ones. The reaction mechanism was proposed and the products were screened for their biological activity. Some of the newly synthesized compounds had a moderate effect against some bacterial and fungal species.

  DOI：

  10.1007/s00706-008-0060-z

文献信息

• A facile one-pot synthesis of 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones
  作者：Sobhi M. Gomha

  DOI：10.1007/s00706-008-0060-z

  日期：2009.2

  The reaction of 2-mercapto-6,7,8,9-tetrahydro3H-benzo[4,5]thieno[2,3- d] pyrimidin-4-one or its 2-methylthio derivative with hydrazonoyl halides, in the presence of triethylamine, yielded 6,7,8,9-tetrahydrobenzo[4,5] thieno [2,3- d]-1,2,4-triazolo[4,5-a] pyrimidin-5-ones. The structure of the latter compounds was further confirmed by reaction of 2-mercapto-6,7,8,9-tetrahydro-3H- benzo[4,5] thieno[2,3- d] pyrimidin-4-one with the appropriate active chloromethylenes followed by coupling of the products with benzenediazonium chloride to afford the non-isolable azocoupling products which converted, in situ, to 6,7,8, 9-tetrahydrobenzo[4,5] thieno[2,3- d]-1,2,4-triazolo[4,5- a] pyrimidin- 5- ones. The reaction mechanism was proposed and the products were screened for their biological activity. Some of the newly synthesized compounds had a moderate effect against some bacterial and fungal species.