2-ethylpyrido[1,2-a][1,2,4]triazol-3-thione | 1067245-14-0

• 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: 2-ethylpyrido[1,2-a][1,2,4]triazol-3-thione
• 英文别名: 2-ethylpyrido[1,2-c][1,2,4]triazol-3-thione；2-Ethyl-pyrido[1,2-a][1,2,4]-triazol-3-thione；2-ethyl-[1,2,4]triazolo[4,3-a]pyridine-3-thione
• CAS: 1067245-14-0
• 化学式: C₈H₉N₃S
• 分子量: 179.246
• InChiKey: FUSMYOQPSUHKPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  50.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-ethyl-[1,2,4] triazolo[4,3-a]pyridin-2-ium tetrafluoroborate 在 sodium hydride 、 sulfur 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.5h， 以95%的产率得到2-ethylpyrido[1,2-a][1,2,4]triazol-3-thione
  参考文献：
  名称：

  Pyrido[1,2-c][1,2,4]triazol-3-ylidene: reactivity and its application in organocatalysis and organometallic catalysis

  摘要：

  2-乙基吡啶并[1,2-c][1,2,4]三唑-3-亚基6的反应性和催化性能已经得到了全面的探究。由于吡啶并环的影响，卡宾6展现出了不寻常的性质。在破坏卡宾的三唑骨架后，得到了福莫肼8和肼9，而通过吡啶环C-N键的断裂，获得了3-((1Z,3E)-4-(1H-吡咯-1-基)丁-1,3-二烯基)-1-乙基-1H-1,2,4-三唑10。卡宾6被证明在多种有机催化和小二催化（Pd(II)催化）反应中是一种强大的催化剂。

  DOI：

  10.1039/b910073c

文献信息

• Pyrido[1,2-<i>a</i>][1,2,4]triazol-3-ylidenes as a New Family of Stable Annulated <i>N</i>-Heterocyclic Carbenes: Synthesis, Reactivity, and Their Application in Coordination Chemistry and Organocatalysis
  作者：Yajun Ma、Siping Wei、Jingbo Lan、Jingzhi Wang、Rugang Xie、Jingsong You

  DOI：10.1021/jo801349d

  日期：2008.11.7

  General synthetic avenues to the pyrido-annulated triazolium salts with different steric and electronic properties have been developed. This architecture can be readily altered with different N-alkyl or aryl substituents at the N2 position of the triazole ring and modifications to the pyridine backbone. Deprotonation of the triazolium salts 12 with NaH led to formation of stable carbenes 11 at room temperature as clearly demonstrated through ESI mass spectra and by observation of the characteristic C-13 NMR resonance for the carbene carbon at delta = 202-208 ppm. In sharp contrast, treatment of these triazolium salts with K2CO3 led to dimerization of free carbenes 11. The dimeric enetetramine (11b)(2) Could react with elemental sulfur to deliver the corresponding thiourea 16 in toluene at 80 degrees C in good yield. A silver complex with the pyrido[1,2-a][1,2,4]triazol-3-ylidene is described, and the molecular structure of complex 17 was established by X-ray crystallography. The triazolium salts 12 turned out to be powerful catalysts in catalytic benzoin condensations and transesterifications at 25 degrees C. The catalytic activity was largely dependent on the steric and electronic nature of the R-1 and R-2 substituents of the triazolium salt. We rationalized that this type of triazolium-catalyzed benzoin condensations should undergo the "traditional" Breslow mechanism rather than the pathway of the dimer (11)(2) as the real catalytic species.