diethyl 5-benzyl-5H-pyrimido[5,4-b]indole-2,4-dicarboxylate | 1438393-63-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: diethyl 5-benzyl-5H-pyrimido[5,4-b]indole-2,4-dicarboxylate
• 英文别名: Diethyl 5-benzylpyrimido[5,4-b]indole-2,4-dicarboxylate；diethyl 5-benzylpyrimido[5,4-b]indole-2,4-dicarboxylate
• CAS: 1438393-63-5
• 化学式: C₂₃H₂₁N₃O₄
• 分子量: 403.437
• InChiKey: KWSMNCXVCUKAAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 5-benzyl-5H-pyrimido[5,4-b]indole-2,4-dicarboxylate 在 盐酸 、 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.0h， 生成 (5-benzyl-5H-pyrimido[5,4-b]indol-4-yl)methanol
  参考文献：
  名称：

  Total Synthesis of 4-Azaeudistomin Y1 and Analogues by Inverse-Electron­Demand Diels-Alder Reactions of 3-Aminoindoles with 1,3,5-Triazines

  摘要：

  A new inverse-electron-demand Diels-Alder (IDA) reaction of 3-aminoindoles as dienophiles was developed for the efficient preparation of 4-aza-beta-carbolines in high yields. Because N-1-unprotected 3-aminoindoles show poor thermal stability, a one-pot protocol was developed that combines the removal of tert-butoxycarbonyl protecting groups with the IDA reaction. This protocol, using tert-butyl 1H-indol-3-ylcarbamates as reactants, gave the corresponding IDA products in excellent yields. The new IDA methodology was used in a total synthesis of 4-azaeudistomin Y-1, which was obtained in 57% overall yield in four steps. Moreover, the chemistry is suitable for the rapid preparation, through either Friedel-Crafts acylation or amide-formation reactions, of analogues that are useful for exploring structure-activity relationships at the C-1-position.

  DOI：

  10.1055/s-0032-1316857
• 作为产物：
  描述：

  1-苄基吲哚-3-甲酸 在 盐酸 、 叠氮磷酸二苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 diethyl 5-benzyl-5H-pyrimido[5,4-b]indole-2,4-dicarboxylate
  参考文献：
  名称：

  Total Synthesis of 4-Azaeudistomin Y1 and Analogues by Inverse-Electron­Demand Diels-Alder Reactions of 3-Aminoindoles with 1,3,5-Triazines

  摘要：

  A new inverse-electron-demand Diels-Alder (IDA) reaction of 3-aminoindoles as dienophiles was developed for the efficient preparation of 4-aza-beta-carbolines in high yields. Because N-1-unprotected 3-aminoindoles show poor thermal stability, a one-pot protocol was developed that combines the removal of tert-butoxycarbonyl protecting groups with the IDA reaction. This protocol, using tert-butyl 1H-indol-3-ylcarbamates as reactants, gave the corresponding IDA products in excellent yields. The new IDA methodology was used in a total synthesis of 4-azaeudistomin Y-1, which was obtained in 57% overall yield in four steps. Moreover, the chemistry is suitable for the rapid preparation, through either Friedel-Crafts acylation or amide-formation reactions, of analogues that are useful for exploring structure-activity relationships at the C-1-position.

  DOI：

  10.1055/s-0032-1316857

文献信息

• Total Synthesis of 4-Azaeudistomin Y1 and Analogues by Inverse-Electron­Demand Diels-Alder Reactions of 3-Aminoindoles with 1,3,5-Triazines
  作者：Qun Dang、Xu Bai、Guoxing Xu、Lianyou Zheng

  DOI：10.1055/s-0032-1316857

  日期：——

  A new inverse-electron-demand Diels-Alder (IDA) reaction of 3-aminoindoles as dienophiles was developed for the efficient preparation of 4-aza-beta-carbolines in high yields. Because N-1-unprotected 3-aminoindoles show poor thermal stability, a one-pot protocol was developed that combines the removal of tert-butoxycarbonyl protecting groups with the IDA reaction. This protocol, using tert-butyl 1H-indol-3-ylcarbamates as reactants, gave the corresponding IDA products in excellent yields. The new IDA methodology was used in a total synthesis of 4-azaeudistomin Y-1, which was obtained in 57% overall yield in four steps. Moreover, the chemistry is suitable for the rapid preparation, through either Friedel-Crafts acylation or amide-formation reactions, of analogues that are useful for exploring structure-activity relationships at the C-1-position.