N-(3-(3-cyano-5-methyl-2-oxo-2,3-dihydro-1H-pyrrol-1-yl)-4-methylthiazol-2(3H)-ylidene)benzamide

• 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: N-(3-(3-cyano-5-methyl-2-oxo-2,3-dihydro-1H-pyrrol-1-yl)-4-methylthiazol-2(3H)-ylidene)benzamide
• 化学式: C₁₇H₁₄N₄O₂S
• 分子量: 338.39
• InChiKey: GOLFXSJTSKJPEI-ZPHPHTNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  78.46
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-cyanoacetyl-4-benzoylthiosemicarbazide 、 溴丙酮 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以86%的产率得到N-(3-(3-cyano-5-methyl-2-oxo-2,3-dihydro-1H-pyrrol-1-yl)-4-methylthiazol-2(3H)-ylidene)benzamide
  参考文献：
  名称：

  Heterocyclic Synthesis with 4-Benzoyl-1-cyanoacetylthiosemicarbazide: Selective Synthesis of Some Thiazole, Triazole, Thiadiazine, Pyrrylthiazole, and Pyrazolo[1,5-a]triazine Derivatives

  摘要：

  4-Benzoyl-1-cyanoacetylthiosemicarbazide undergoes coupling reaction with aromatic diazonium chloride to afford (arylhydrazono)thiosemicarbazide, which was reacted with phenacyl bromide regioselectivity to afford the thiazoline. The (arylhydrazono)thiosemicarbazide could be transformed into the pyrazolo[1,5-a]triazine. Heterocyclization of 4-benzoyl-1-cyanoacetylthiosemicarbazide with alpha-haloketones (bromoacetone and phenacyl bromide), ethyl iodide, and ethyl bromoacetate furnished the pyrrylthiazoles, 1,2,4- triazole, and 1,3,4-thiadiazine. The latter was coupled with aromatic diazonium chloride to give the bis(arylhydrazono)-thiadiazine. The mechanism for the formation of the title compounds was suggested and discussed.

  DOI：

  10.1007/s00706-007-0764-5

文献信息

• Heterocyclic Synthesis with 4-Benzoyl-1-cyanoacetylthiosemicarbazide: Selective Synthesis of Some Thiazole, Triazole, Thiadiazine, Pyrrylthiazole, and Pyrazolo[1,5-a]triazine Derivatives
  作者：Samir Bondock、Abd El-Gaber Tarhoni、Ahmed A. Fadda

  DOI：10.1007/s00706-007-0764-5

  日期：2008.2

  4-Benzoyl-1-cyanoacetylthiosemicarbazide undergoes coupling reaction with aromatic diazonium chloride to afford (arylhydrazono)thiosemicarbazide, which was reacted with phenacyl bromide regioselectivity to afford the thiazoline. The (arylhydrazono)thiosemicarbazide could be transformed into the pyrazolo[1,5-a]triazine. Heterocyclization of 4-benzoyl-1-cyanoacetylthiosemicarbazide with alpha-haloketones (bromoacetone and phenacyl bromide), ethyl iodide, and ethyl bromoacetate furnished the pyrrylthiazoles, 1,2,4- triazole, and 1,3,4-thiadiazine. The latter was coupled with aromatic diazonium chloride to give the bis(arylhydrazono)-thiadiazine. The mechanism for the formation of the title compounds was suggested and discussed.