N-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-amine | 28539-20-0

• 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-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-amine
• CAS: 28539-20-0
• 化学式: C₁₂H₁₀N₄
• 分子量: 210.238
• InChiKey: OXWSFEYLUIEUKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 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：

  1-α-pyridylamino-3 phenyl-2 thiourea 在 2-碘苯甲酸 、 tetrabutylammonium tetrafluoroborate 、 sodium chloride 作用下， 以 乙腈 为溶剂， 以79 %的产率得到N-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-amine
  参考文献：
  名称：

  硫脲电催化脱硫胺化制胍

  摘要：

  胍被认为是一类重要的含氮分子，具有广泛的应用。这里描述的是一种选择性且有效的电化学方法，用于从容易获得的硫脲和胺合成胍。该反应成功的关键是通过阳极氧化从碘芳烃中原位生成高价碘试剂作为催化剂。这种温和的脱硫胺化具有充足的底物范围和良好的官能团耐受性，无需使用额外的化学计量化学氧化剂。由于只有电子作为氧化试剂，该方法为多功能胍提供了更直接和可持续的方式，包括药物相关分子的后期功能化。

  DOI：

  10.1021/acs.joc.3c01612

文献信息

• 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。
• 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。
• I₂-Mediated Oxidative C–N and N–S Bond Formation in Water: A Metal-Free Synthesis of 4,5-Disubstituted/N-Fused 3-Amino-1,2,4-triazoles and 3-Substituted 5-Amino-1,2,4-thiadiazoles
  作者：Nagesh Jatangi、Nagaraju Tumula、Radha Krishna Palakodety、Mangarao Nakka

  DOI：10.1021/acs.joc.8b00753

  日期：2018.5.18

  environmentally benign and convenient strategy for the synthesis of 4,5-disubstituted/N-fused 3-amino-1,2,4-triazoles and 3-substituted 5-amino-1,2,4-thiadiazoles from isothiocyanates has been developed. This metal-free method involves I2-mediated oxidative C–N and N–S bond formations in water. Furthermore, this facile protocol exhibited excellent substrate tolerance in good to high yields and scalable fashion

  从异硫氰酸酯合成4，5-二取代/ N稠合的3-氨基-1,2,4-三唑和3-取代的5-氨基-1,2,4-噻二唑的环境友好，方便的策略已得到开发。 。这种无金属方法涉及水中I 2介导的氧化性C–N和N–S键的形成。此外，这种简便的方案以良好的高产量和可扩展的方式表现出出色的基材耐受性。
• 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。
• 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.