N-(tert-octyl)[1,2,4]triazolo[4,3-a]pyridin-3-amine | 1174271-67-0

• 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: N-(tert-octyl)[1,2,4]triazolo[4,3-a]pyridin-3-amine
• 英文别名: N-(2,4,4-trimethylpentan-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-amine
• CAS: 1174271-67-0
• 化学式: C₁₄H₂₂N₄
• 分子量: 246.355
• InChiKey: BURAZJZPHINYAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-tert-octyl-2-pyridin-2-ylhydrazinecarbothioamide 在 三乙胺 、 甲醇 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以81%的产率得到N-(tert-octyl)[1,2,4]triazolo[4,3-a]pyridin-3-amine
  参考文献：
  名称：

  A Straightforward, One-Pot Protocol for the Synthesis of Fused 3-Aminotriazoles

  摘要：

  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.

  DOI：

  10.1021/jo9009084

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.