5-carboxamido-6-(methylthio)pyrrolo[2,3-d][1,2,3]triazin-4-one | 355375-81-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5-carboxamido-6-(methylthio)pyrrolo[2,3-d][1,2,3]triazin-4-one
• 英文别名: 6-Methylsulfanyl-4-oxo-3,7-dihydropyrrolo[2,3-d]triazine-5-carboxamide
• CAS: 355375-81-4
• 化学式: C₇H₇N₅O₂S
• 分子量: 225.231
• InChiKey: ZHWFENCTVOQMJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  138
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-carboxamido-6-(methylthio)pyrrolo[2,3-d][1,2,3]triazin-4-one 在 氢氧化钾 、 双氧水 作用下， 以 水 为溶剂， 反应 4.0h， 以67%的产率得到5-carboxamido-6-sulfinylpyrrolo[2,3-d][1,2,3]triazin-4-one
  参考文献：
  名称：

  Synthesis and Unusual Chemical Reactivity of Certain Novel 4,5-Disubstituted 7-Benzylpyrrolo[2,3-d][1,2,3]triazines

  摘要：

  The fact that only two pyrrolo[2,3-d] [1,2,3]triazines heterocycles had been reported in the literature prompted us to initiate studies designed to provide additional members of this ring system. Initial attempts to prepare additional derivatives of the 7-unsubstituted pyrrolo[2,3-d] [1,2,3]triazin-4-ones were limited by their low chemical reactivity. Subsequently, 7-benzyl-5-carboxamidopyrrololo-,3-d] [1,2,3]triazin-4-one (16) was prepared from diethyl 2-nitropyrrole-3,4,-dicarboxylate via an alkylation, ammonolysis, reduction and intramolecular diazocoupling sequence. Conversion of 16 into 7-benzyl-4-( 1,2,4-triazol-1-yl)pyrrolo [2,3-d] [1,2,3]triazine-5-carbonitrile (17) was accomplished, and nucleophilic displacements of the 4-triazol-1- yl group were studied. Treatment of 17 with NH3/CH3CN gave a mixture of 4-amino-7-benzylpyrrolo [2,3-d] [1,2,3] triazine-5-carbonitrile (19) and 2-amino-1-benzylpyrrole-3,4-dicarbonitrile (21), A mechanism to account for the formation of this mixture is described along with studies on the effect that ammonia concentration and a TFA catalyst have on the product ratio. Compound 19 was converted into the 5-carboxamide and 5-thioamide derivatives of 19.

  DOI：

  10.1021/jo001499i
• 作为产物：
  描述：

  2-氨基-5-甲基硫代-(1h)-吡咯-3,4-二羧酰胺 在 亚硝酸特丁酯 作用下， 以 水 、 溶剂黄146 为溶剂， 以45%的产率得到5-carboxamido-6-(methylthio)pyrrolo[2,3-d][1,2,3]triazin-4-one
  参考文献：
  名称：

  Synthesis and Unusual Chemical Reactivity of Certain Novel 4,5-Disubstituted 7-Benzylpyrrolo[2,3-d][1,2,3]triazines

  摘要：

  The fact that only two pyrrolo[2,3-d] [1,2,3]triazines heterocycles had been reported in the literature prompted us to initiate studies designed to provide additional members of this ring system. Initial attempts to prepare additional derivatives of the 7-unsubstituted pyrrolo[2,3-d] [1,2,3]triazin-4-ones were limited by their low chemical reactivity. Subsequently, 7-benzyl-5-carboxamidopyrrololo-,3-d] [1,2,3]triazin-4-one (16) was prepared from diethyl 2-nitropyrrole-3,4,-dicarboxylate via an alkylation, ammonolysis, reduction and intramolecular diazocoupling sequence. Conversion of 16 into 7-benzyl-4-( 1,2,4-triazol-1-yl)pyrrolo [2,3-d] [1,2,3]triazine-5-carbonitrile (17) was accomplished, and nucleophilic displacements of the 4-triazol-1- yl group were studied. Treatment of 17 with NH3/CH3CN gave a mixture of 4-amino-7-benzylpyrrolo [2,3-d] [1,2,3] triazine-5-carbonitrile (19) and 2-amino-1-benzylpyrrole-3,4-dicarbonitrile (21), A mechanism to account for the formation of this mixture is described along with studies on the effect that ammonia concentration and a TFA catalyst have on the product ratio. Compound 19 was converted into the 5-carboxamide and 5-thioamide derivatives of 19.

  DOI：

  10.1021/jo001499i