3-ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole | 223589-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole
• 英文别名: 2-(5-Ethylsulfanyl-4-phenyl-1,2,4-triazol-3-yl)acetonitrile
• CAS: 223589-66-0
• 化学式: C₁₂H₁₂N₄S
• 分子量: 244.32
• InChiKey: RJQAXCHRXXBHIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  79.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole 在 sodium acetate 、 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl 4-amino-3-(5-ethylthio-4-phenyl-4H-1,2,4-triazol-3-yl)-1-(4-methylphenyl)-1H-pyrazole-5-carboxylate
  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：

  Sodium; [(2-cyano-acetyl)-hydrazono]-phenylamino-methanethiolate 在 盐酸 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-ethylthio-5-cyanomethyl-4-phenyl-1,2,4-triazole
  参考文献：
  名称：

  Mekheimer, Ramadan A.; Shaker, Rafat M., Journal of Chemical Research, Miniprint, 1999, # 2, p. 449 - 459

  摘要：

  DOI：

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。
• Naphthyridines. Part 3: First example of the polyfunctionally substituted 1,2,4-triazolo[1,5-g][1,6]naphthyridines ring system
  作者：Ramadan Ahmed Mekheimer、Yusria Rizk Ibrahim、Eltaib Ali Ahmed、Wolfgang Frey

  DOI：10.1016/j.tet.2009.09.082

  日期：2009.11

  Treatment of 1,2,4-triazoles (1) with diethylmalonate in bromobenzene gave 1,2,4-triazolo-[1,5-a]pyridines 2. Chlorination of 2 using POCl3/DMF (Vilsmeier reagent) led to the isolation of 7-chloro-6-formyl-1,2,4-triazolo[1,5-a]pyridine derivative 4, which reacted with the stabilized ylid 5 to afford 6-ethoxycarbonylvinyl-1,2,4-triazolo[1,5-a]-pyridines 6. Azidation of 6 yielded the corresponding azido

  在溴苯中用丙二酸二乙酯处理1,2,4-三唑（1），得到1,2,4-三唑-[1,5- a ]吡啶2。使用POCl 3 / DMF（Vilsmeier试剂）氯化2导致分离7-氯-6-甲酰基-1,2,4-三唑并[1,5- a ]吡啶衍生物4，该衍生物与稳定的碘5反应 得到6-乙氧基羰基乙烯基-1，2，4-三唑并[1，5- a ]-吡啶6。叠氮化6产生相应的叠氮基化合物7，（方案2）。用Na 2 S 2 O还原74得到相应的7-氨基化合物8，其在沸腾的DMF中环化，得到新的1,2,4-三唑并[1,5- g ] [1,6]萘啶9。另一方面，使7与1当量的PPh 3（氮杂-维蒂希反应）在CH 2 Cl 2中反应，得到7-亚氨基-膦烷衍生物10，随后在沸腾的DMF中环化，得到新的1,2,4-三唑并[ 1,5- g ] [1,6]萘啶衍生物11（方案3）。然而，在回流温度下，在1,2-二氯苯中用异硫氰酸苯酯处理10，得到新的1