7-methoxy-3-(4-chlorophenyl)-1H-pyrimido[5,4-b]-indole-2,4(3H,5H)-dione | 1030553-85-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 7-methoxy-3-(4-chlorophenyl)-1H-pyrimido[5,4-b]-indole-2,4(3H,5H)-dione
• 英文别名: 3-(4-chlorophenyl)-7-methoxy-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-dione；3-(4-chlorophenyl)-7-methoxy-1,5-dihydropyrimido[5,4-b]indole-2,4-dione
• CAS: 1030553-85-5
• 化学式: C₁₇H₁₂ClN₃O₃
• 分子量: 341.754
• InChiKey: FEXXDVZRMKULIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  74.4
• 氢给体数：
  2
• 氢受体数：
  3

上下游信息

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	1,5-dimethyl-7-methoxy-3-(4-chlorophenyl)-1H-pyrimido[5,4-b]-indole-2,4(3H,5H)-dione	1030575-34-8	C19H16ClN3O3	369.807

反应信息

• 作为反应物：
  描述：

  7-methoxy-3-(4-chlorophenyl)-1H-pyrimido[5,4-b]-indole-2,4(3H,5H)-dione 、 碘甲烷 在 sodium methylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以69%的产率得到1,5-dimethyl-7-methoxy-3-(4-chlorophenyl)-1H-pyrimido[5,4-b]-indole-2,4(3H,5H)-dione
  参考文献：
  名称：

  Methyl 3-amino-1H-indole-2-carboxylates in the synthesis of 5H-pyrimido[5,4-b]indole derivatives

  摘要：

  Reactions of methyl 3-amino-1H-indole-2-carboxylates with aryl isocyanates, aryl isothiocyanates, and cyanamides led to the formation of 5H-pyrimido[5,4-b]indole derivatives. In the reaction with isocyanates formed 3-aryl-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-diones that were involved into the alkylation at two nitrogen atoms. The reaction with isothiocyanates afforded 3-aryl-2-thioxo-2,3-dihydro-1H-pyrimido[5,4-b]indol-4(5H)-ones undergoing alkylation at the sulfur atom. The reactions with benzoylcyanamide and N-(4,6-dimethylpyrimidin-2-yl)cyanamide resulted in N-(4-oxo-4,5-dihydro-3H-pyrimido-[5,4-b]indol-2-yl)benzamides and 2-(4,6-dimethylpyrimidin-2-ylamino)-3H-pyrimido[5,4-b]indol-4(5H)-ones respectively.

  DOI：

  10.1134/s1070428009050224
• 作为产物：
  描述：

  methyl 6-methoxy-3-[3-(4-chlorophenyl)ureido]-1H-indole-2-carboxylate 在 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 5.0h， 以95%的产率得到7-methoxy-3-(4-chlorophenyl)-1H-pyrimido[5,4-b]-indole-2,4(3H,5H)-dione
  参考文献：
  名称：

  Methyl 3-amino-1H-indole-2-carboxylates in the synthesis of 5H-pyrimido[5,4-b]indole derivatives

  摘要：

  Reactions of methyl 3-amino-1H-indole-2-carboxylates with aryl isocyanates, aryl isothiocyanates, and cyanamides led to the formation of 5H-pyrimido[5,4-b]indole derivatives. In the reaction with isocyanates formed 3-aryl-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-diones that were involved into the alkylation at two nitrogen atoms. The reaction with isothiocyanates afforded 3-aryl-2-thioxo-2,3-dihydro-1H-pyrimido[5,4-b]indol-4(5H)-ones undergoing alkylation at the sulfur atom. The reactions with benzoylcyanamide and N-(4,6-dimethylpyrimidin-2-yl)cyanamide resulted in N-(4-oxo-4,5-dihydro-3H-pyrimido-[5,4-b]indol-2-yl)benzamides and 2-(4,6-dimethylpyrimidin-2-ylamino)-3H-pyrimido[5,4-b]indol-4(5H)-ones respectively.

  DOI：

  10.1134/s1070428009050224

文献信息

• Methyl 3-amino-1H-indole-2-carboxylates in the synthesis of 5H-pyrimido[5,4-b]indole derivatives
  作者：A. S. Shestakov、Kh. S. Shikhaliev、O. E. Sidorenko、V. G. Kartsev、S. V. Simakov

  DOI：10.1134/s1070428009050224

  日期：2009.5

  Reactions of methyl 3-amino-1H-indole-2-carboxylates with aryl isocyanates, aryl isothiocyanates, and cyanamides led to the formation of 5H-pyrimido[5,4-b]indole derivatives. In the reaction with isocyanates formed 3-aryl-1H-pyrimido[5,4-b]indole-2,4(3H,5H)-diones that were involved into the alkylation at two nitrogen atoms. The reaction with isothiocyanates afforded 3-aryl-2-thioxo-2,3-dihydro-1H-pyrimido[5,4-b]indol-4(5H)-ones undergoing alkylation at the sulfur atom. The reactions with benzoylcyanamide and N-(4,6-dimethylpyrimidin-2-yl)cyanamide resulted in N-(4-oxo-4,5-dihydro-3H-pyrimido-[5,4-b]indol-2-yl)benzamides and 2-(4,6-dimethylpyrimidin-2-ylamino)-3H-pyrimido[5,4-b]indol-4(5H)-ones respectively.