5-chloro-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-amine | 1174271-86-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-chloro-N-(4-(trifluoromethyl)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3-amine
• 英文别名: N-(4-trifluoromethylphenyl)-5-chloro[1,2,4]triazolo[4,3-a]pyridin-3-amine；5-chloro-N-[4-(trifluoromethyl)phenyl]-[1,2,4]triazolo[4,3-a]pyridin-3-amine
• CAS: 1174271-86-3
• 化学式: C₁₃H₈ClF₃N₄
• 分子量: 312.682
• InChiKey: UKLPKIKHAZNOJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(6-chloropyridin-2-yl)-N-(4-(trifluoromethyl)phenyl)hydrazinecarbothioamide 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72%的产率得到5-chloro-N-(4-(trifluoromethyl)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

• Supramolecular Anion Recognition Mediates One-Pot Synthesis of 3-Amino-[1,2,4]-triazolo Pyridines from Thiosemicarbazides
  作者：Komala Pandurangan、Anna B. Aletti、Devis Montroni、Jonathan. A. Kitchen、Miguel Martínez-Calvo、Salvador Blasco、Thorfinnur Gunnlaugsson、Eoin M. Scanlan

  DOI：10.1021/acs.orglett.6b03645

  日期：2017.3.3

  A facile one-pot synthesis of 3-amino-[1,2,4]-triazolo[4,3-a]pyridines from thiosemicarbazides through anion mediated synthesis is reported. Thiosemicarbazides derived from 2-hydrazino pyridine, 5-chloro 2-hydrazino pyridine, and 2-hydrazine quinoline were formed in situ as anion receptors in the presence of TBAF. Under microwave heating, thiosemicarbazides furnished the triazolo pyridines in good

  据报道，通过阴离子介导的合成，从硫代氨基脲容易地一锅合成3-氨基-[1,2,4]-三唑并[4,3- a ]吡啶。在TBAF存在下原位形成衍生自2-肼基吡啶，5-氯2-肼基吡啶和2-肼基喹啉的硫代氨基脲作为阴离子受体。在微波加热下，硫代氨基脲以良好至中等的产率提供了三唑并吡啶。硫代氨基脲氢键阴离子受体的形成对于级联三唑并吡啶的反应至关重要。
• 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.