2-(5-ethylthio-4-phenyl-4H-[1,2,4-]-triazol-3-yl)-2-(phenylhydrazono)acetonitrile | 1596326-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(5-ethylthio-4-phenyl-4H-[1,2,4-]-triazol-3-yl)-2-(phenylhydrazono)acetonitrile
• 英文别名: N-anilino-5-ethylsulfanyl-4-phenyl-1,2,4-triazole-3-carboximidoyl cyanide
• CAS: 1596326-80-5
• 化学式: C₁₈H₁₆N₆S
• 分子量: 348.431
• InChiKey: DODRSZCARYZBNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(5-ethylthio-4-phenyl-4H-[1,2,4-]-triazol-3-yl)-2-(phenylhydrazono)acetonitrile 在 硫酸 、 potassium carbonate 、 sodium nitrite 作用下， 以 melt 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.03h， 生成 6-bromo-3-(5-ethylthio-4-phenyl-4H-1,2,4-triazol-3-yl)-1-phenyl-1H-pyrazolo[4,3-b]quinolin-9(4H)-one
  参考文献：
  名称：

  A Novel Synthesis of 1-Aryl-6-bromo-3-(5-ethylthio-4-phenyl-4H-1,2,4-triazol-3-yl)-1H-pyrazolo[4,3-b]quinolin-9(4H)-onesviaThermal Cyclization of 4-Azidopyrazoles

  摘要：

  2‐Aryl‐hydrazononitriles 3a, 3b, 3c were prepared by coupling 3‐ethylthio‐5‐cyanomethyl‐4‐phenyl‐1,2,4‐triazole (1) with diazonium salts 2a, 2b, 2c. Reacting 3a, 3b, 3c with both ethyl bromoacetate (4a) and 4‐bromobenzyl bromide (4b) in DMF, in the presence of K2CO3, at 80 °C for 3–4 h, gave the corresponding 4‐amino‐pyrazoles 6a, 6b, 6c, 6d, 6e, 6f. Diazotization of 6a, 6b, 6c, 6d, 6e, 6f, followed by reaction with NaN3, leads to the formation of 4‐azidopyrazoles 8a, 8b, 8c, 8d, 8e, 8f, a new heterocyclic ring system. Interestingly, fusion of 4‐azidopyrazoles 8d, 8e, 8f at temperature higher than their melting points with 5 °C for 2 min did not give the expected fused pyrazolo[4,3‐c]isoxazoles 9 but furnished instead the novel pyrazolo[4,3‐b]quinolinones 10a, 10b, 10c, in high yields.

  DOI：

  10.1002/jhet.2363
• 作为产物：
  描述：

  aniline hydrochloride 、 3-ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole 在 sodium nitrite 、 sodium acetate 作用下， 以 水 、 乙醇 为溶剂， 反应 24.0h， 以90%的产率得到2-(5-ethylthio-4-phenyl-4H-[1,2,4-]-triazol-3-yl)-2-(phenylhydrazono)acetonitrile
  参考文献：
  名称：

  Synthesis and Spectroscopic Properties of New Azo Dyes Derived from 3-Ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole

  摘要：

  通过将 3-乙硫基-5-氰甲基-4-苯基-1,2,4-三唑（1）与重氮化苯胺衍生物 2、4 和 6 偶联，高产率地获得了新的 1,2,4-三唑着色剂。这项工作中制备的偶氮染料可能以三种同分异构形式存在。我们发现，同分异构主要受苯胺偶联组分对位取代基性质的影响。我们在染料的核磁共振光谱中观察到了这种同分异构现象。这些染料通过红外光谱、1H-NMR、13C-NMR 和 MS 光谱技术进行了表征。

  DOI：

  10.3390/molecules19032993

文献信息

• Synthesis and Spectroscopic Properties of New Azo Dyes Derived from 3-Ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole
  作者：Mariam Al-Sheikh、Hanadi Y. Medrasi、Kamal Usef Sadek、Ramadan Ahmed Mekheimer

  DOI：10.3390/molecules19032993

  日期：——

  New 1,2,4-triazole colorants were obtained, in high yields, by coupling 3-ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole (1) with diazotized aniline derivatives 2, 4 and 6. The azo dyes prepared in this work may exist in three tautomeric forms. We found that the tautomerism is influenced mainly by the nature of substituent at the para position of the aniline coupling component. This tautomerisation was observed in the NMR spectra of the dyes. The dyes were characterized by IR, 1H-NMR, 13C-NMR and MS spectroscopic techniques.

  通过将 3-乙硫基-5-氰甲基-4-苯基-1,2,4-三唑（1）与重氮化苯胺衍生物 2、4 和 6 偶联，高产率地获得了新的 1,2,4-三唑着色剂。这项工作中制备的偶氮染料可能以三种同分异构形式存在。我们发现，同分异构主要受苯胺偶联组分对位取代基性质的影响。我们在染料的核磁共振光谱中观察到了这种同分异构现象。这些染料通过红外光谱、1H-NMR、13C-NMR 和 MS 光谱技术进行了表征。
• A Novel Synthesis of 1-Aryl-6-bromo-3-(5-ethylthio-4-phenyl-4<i>H</i>-1,2,4-triazol-3-yl)-1<i>H</i>-pyrazolo[4,3-<i>b</i>]quinolin-9(4<i>H</i>)-ones<i>via</i>Thermal Cyclization of 4-Azidopyrazoles
  作者：Hanadi Y. Medrasi、Mariam Al-Sheikh、Kamal Usef Sadek、Ramadan Ahmed Mekheimer

  DOI：10.1002/jhet.2363

  日期：2016.7

  2‐Aryl‐hydrazononitriles 3a, 3b, 3c were prepared by coupling 3‐ethylthio‐5‐cyanomethyl‐4‐phenyl‐1,2,4‐triazole (1) with diazonium salts 2a, 2b, 2c. Reacting 3a, 3b, 3c with both ethyl bromoacetate (4a) and 4‐bromobenzyl bromide (4b) in DMF, in the presence of K2CO3, at 80 °C for 3–4 h, gave the corresponding 4‐amino‐pyrazoles 6a, 6b, 6c, 6d, 6e, 6f. Diazotization of 6a, 6b, 6c, 6d, 6e, 6f, followed by reaction with NaN3, leads to the formation of 4‐azidopyrazoles 8a, 8b, 8c, 8d, 8e, 8f, a new heterocyclic ring system. Interestingly, fusion of 4‐azidopyrazoles 8d, 8e, 8f at temperature higher than their melting points with 5 °C for 2 min did not give the expected fused pyrazolo[4,3‐c]isoxazoles 9 but furnished instead the novel pyrazolo[4,3‐b]quinolinones 10a, 10b, 10c, in high yields.