5-chloro-N-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-amine | 1174271-82-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并哒嗪类
• 英文名称: 5-chloro-N-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-amine
• 英文别名: N-(phenyl)-5-chloro[1,2,4]triazolo[4,3-a]pyridin-3-amine
• CAS: 1174271-82-9
• 化学式: C₁₂H₉ClN₄
• 分子量: 244.683
• InChiKey: QXWZNRAKEBOEGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  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 2.0h， 以78%的产率得到5-chloro-N-phenyl-[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

• Access to 3-Amino-[1,2,4]-triazolo Pyridines and Related Heterocycles via Electrochemically Induced Desulfurative Cyclization
  作者：Yunfei Hu、Li Chen、Canlin Zou、Jiangtao He、Luanqi Feng、Jia-Qiang Wu、Wen-Hua Chen、Jinhui Hu

  DOI：10.1021/acs.orglett.2c01968

  日期：2022.7.22

  An efficient, one-pot approach has been established for synthesizing a wide range of 3-amino-[1,2,4]-triazolo pyridines and related heterocycles from the electrochemically induced desulfurative cyclization of 2-hydrazinopyridines with isothiocyanates. The protocol allows for the formation of C–N bonds under simple conditions without transition metals or external oxidants. The practicability of this

  已经建立了一种有效的一锅法，用于通过电化学诱导的 2-肼基吡啶与异硫氰酸酯的脱硫环化合成各种 3-氨基-[1,2,4]-三唑并吡啶和相关杂环。该协议允许在没有过渡金属或外部氧化剂的简单条件下形成 C-N 键。该策略的实用性体现在其广泛的底物范围、良好的官能团相容性和克级合成。3-氨基-[1,2,4]-三唑并吡啶的后期修饰使我们能够获得几种具有有效抗癌活性的分子。