ethyl 4-(4-methoxybenzoyl)-5H-pyrimido[5,4-b]indole-2-carboxylate | 1438393-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-(4-methoxybenzoyl)-5H-pyrimido[5,4-b]indole-2-carboxylate
• CAS: 1438393-73-7
• 化学式: C₂₁H₁₇N₃O₄
• 分子量: 375.384
• InChiKey: LBAFBXFXJXDLGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-methoxybenzoyl)-5H-pyrimido[5,4-b]indole-2-carboxylate 在 盐酸 作用下， 以 水 为溶剂， 以40%的产率得到(4-methoxyphenyl)(5H-pyrimido[5,4-b]indol-4-yl)methanone
  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：

  3-吲哚甲酸 在 aluminum (III) chloride 、 sodium tetrahydroborate 、 potassium permanganate 、 草酰氯 、 叠氮磷酸二苯酯 、 三氟化硼乙醚 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 溶剂黄146 为溶剂， 反应 74.0h， 生成 ethyl 4-(4-methoxybenzoyl)-5H-pyrimido[5,4-b]indole-2-carboxylate
  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.