5-(methylthio)-N-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3-amine | 1174271-92-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 5-(methylthio)-N-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3-amine
• 英文别名: 5-methylsulfanyl-N-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3-amine
• CAS: 1174271-92-1
• 化学式: C₁₂H₁₁N₅S
• 分子量: 257.319
• InChiKey: IMHKZAIASIUDDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  在 碘 、 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以102 mg的产率得到5-(methylthio)-N-phenyl-[1,2,4]triazolo[4,3-c]pyrimidin-3-amine
  参考文献：
  名称：

  通过向异硫氰酸酯依次添加芳基肼和I 2介导的环脱硫反应，合成熔融的3-氨基-1,2,4-三唑

  摘要：

  通过将芳基肼加到异硫氰酸酯中，然后进行I 2介导的氧化环脱硫，合成了多种稠合的3-氨基-1,2,4-三唑衍生物。这种无过渡金属的合成方法可轻松，高效地从容易获得的底物中轻松获得1,2,4-三唑并[4,3- a ]吡啶和带有3-氨基取代基的相关杂环骨架。

  DOI：

  10.1016/j.tet.2018.05.009

文献信息

• A Straightforward, One-Pot Protocol for the Synthesis of Fused 3-Aminotriazoles
  作者：Horacio Comas、Gérald Bernardinelli、Dominique Swinnen

  DOI：10.1021/jo9009084

  日期：2009.8.7

  A simple protocol for the synthesis of 3-amino-[1,2,4]triazolo[4,3-a]pyridines is reported. The newly developed one-pot methodology involves the reaction of hydrazinopyridine with isothiocyanates to give the corresponding thiosemicarbazides, which are further desulfurized in situ using polymer-supported Mukaiyama's reagent to promote the final cyclization and formation of the central core. Aryl isothiocyanates bearing both electron-donating and electron-withdrawing groups are well tolerated, and the expected compounds were obtained in excellent purities and yields after removal of salts with a SPE-NH2 column. This methodology proved to be robust in the extension to 3-amino-[1,2,4]triazolo[4,3-a]-pyrazines and 3-amino-[1,2,4]triazolo[4,3-c]-pyrimidines, and no significant differences were noticed in terms of purities and yields. The straightforward protocol developed, mix,filler, and evaporate, is appropriate for performing multiple reactions in parallel fashion without need of purification.
• Synthesis of fused 3-amino-1,2,4-triazoles via sequential addition of aryl hydrazines to isothiocyanates and I 2 -mediated cyclodesulfurization
  作者：Shufeng Jiao、Zhen Wang、Qiongli Zhao、Wenquan Yu、Junbiao Chang

  DOI：10.1016/j.tet.2018.05.009

  日期：2018.6

  A variety of fused 3-amino-1,2,4-triazole derivatives were synthesized via addition of aryl hydrazines to isothiocyanates followed by I2-mediated oxidative cyclodesulfurization. This transition-metal-free synthetic process provides facile access to 1,2,4-triazolo[4,3-a]pyridines and related heterocyclic frameworks bearing a 3-amino substituent from readily accessible substrates in an efficient and

  通过将芳基肼加到异硫氰酸酯中，然后进行I 2介导的氧化环脱硫，合成了多种稠合的3-氨基-1,2,4-三唑衍生物。这种无过渡金属的合成方法可轻松，高效地从容易获得的底物中轻松获得1,2,4-三唑并[4,3- a ]吡啶和带有3-氨基取代基的相关杂环骨架。