1,2-Diamino-5-cyano-6-oxo-1,6-dihydro-pyridine-3,4-dicarboxylic acid diethyl ester | 211688-57-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1,2-Diamino-5-cyano-6-oxo-1,6-dihydro-pyridine-3,4-dicarboxylic acid diethyl ester
• 英文别名: Diethyl 1,2-diamino-5-cyano-6-oxopyridine-3,4-dicarboxylate
• CAS: 211688-57-2
• 化学式: C₁₂H₁₄N₄O₅
• 分子量: 294.267
• InChiKey: WBWOXENSYXUDJX-UHFFFAOYSA-N

物化性质

• 沸点：
  373.394±52.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.434±0.10 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2-Diamino-5-cyano-6-oxo-1,6-dihydro-pyridine-3,4-dicarboxylic acid diethyl ester 在 盐酸 、 sodium azide 、 sodium acetate 、 sodium nitrite 作用下， 以 水 、 丙酮 为溶剂， 以93%的产率得到diethyl 2-amino-5-cyano-6-oxo-1H-pyridine-3,4-dicarboxylate
  参考文献：
  名称：

  A Novel Synthesis of 1,6-Diamino-2-pyridones and [1,2,4]Triazolo-[1,5-a]pyridine Derivatives

  摘要：

  3-Cyano-1,6-diamino-2-pyridone derivatives (3) possessing various alkoxycarbonyl groups are prepared directly from the reaction of dialkyl (E)-2,3-dicyanobutendioates (1) with cyano-acetohydrazide (2). The resulting diamine (3) (R = Et) is readily cyclized to 8-substituted [1,2,4]triazolo[1,5-a]pyridine derivatives (5) in high yields by treatment with orthocarboxylic esters (4) such as trimethyl orthoformate or triethyl orthoacetate etc. Furthermore, 3-cyano-6-amino-2-pyridones (6) are although obtained in excellent yields by the reductive deamination of 3. The structural study of 6 was carried out by spectroscopic methods in some details.

  DOI：

  10.3987/com-98-8136
• 作为产物：
  描述：

  氰乙酰肼 、 (2E)-2,3-二氰基-2-丁烯二酸 1,4-二乙基酯 以 乙腈 为溶剂， 反应 3.0h， 以64%的产率得到1,2-Diamino-5-cyano-6-oxo-1,6-dihydro-pyridine-3,4-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  A Novel Synthesis of 1,6-Diamino-2-pyridones and [1,2,4]Triazolo-[1,5-a]pyridine Derivatives

  摘要：

  3-Cyano-1,6-diamino-2-pyridone derivatives (3) possessing various alkoxycarbonyl groups are prepared directly from the reaction of dialkyl (E)-2,3-dicyanobutendioates (1) with cyano-acetohydrazide (2). The resulting diamine (3) (R = Et) is readily cyclized to 8-substituted [1,2,4]triazolo[1,5-a]pyridine derivatives (5) in high yields by treatment with orthocarboxylic esters (4) such as trimethyl orthoformate or triethyl orthoacetate etc. Furthermore, 3-cyano-6-amino-2-pyridones (6) are although obtained in excellent yields by the reductive deamination of 3. The structural study of 6 was carried out by spectroscopic methods in some details.

  DOI：

  10.3987/com-98-8136

文献信息

• A Novel Synthesis of 1,6-Diamino-2-pyridones and [1,2,4]Triazolo-[1,5-a]pyridine Derivatives
  作者：Yoichi Yamada、Heinosuke Yasuda、Akiko Takayama

  DOI：10.3987/com-98-8136

  日期：——

  3-Cyano-1,6-diamino-2-pyridone derivatives (3) possessing various alkoxycarbonyl groups are prepared directly from the reaction of dialkyl (E)-2,3-dicyanobutendioates (1) with cyano-acetohydrazide (2). The resulting diamine (3) (R = Et) is readily cyclized to 8-substituted [1,2,4]triazolo[1,5-a]pyridine derivatives (5) in high yields by treatment with orthocarboxylic esters (4) such as trimethyl orthoformate or triethyl orthoacetate etc. Furthermore, 3-cyano-6-amino-2-pyridones (6) are although obtained in excellent yields by the reductive deamination of 3. The structural study of 6 was carried out by spectroscopic methods in some details.