5-azido-2-methyl-4-phenylpyridazin-3(2H)-one | 929190-90-9

• 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-azido-2-methyl-4-phenylpyridazin-3(2H)-one
• 英文别名: 5-Azido-2-methyl-4-phenylpyridazin-3-one；5-azido-2-methyl-4-phenylpyridazin-3-one
• CAS: 929190-90-9
• 化学式: C₁₁H₉N₅O
• 分子量: 227.225
• InChiKey: AXQDGDHCDGTPMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-azido-2-methyl-4-phenylpyridazin-3(2H)-one 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以80%的产率得到2-methyl-2,5-dihydro-1H-pyridazino[4,5-b]indol-1-one
  参考文献：
  名称：

  Thermolysis of 5-Azido-4-arylpyridazin-3(2H)-ones: An Efficient and Versatile Synthesis of Pyridazino[4,5-b]indoles

  摘要：

  5-Azido-4-arylpyridazin-3(2H)-ones, which are easily available from 4,5-dihalopyridazin-3(2H)-ones in few steps, were found to undergo in high yields a thermally induced cyclization into pyridazino[4,5-b]indole derivatives ("azacarbolinones") by formation of the N-5/C-5a bond via a nitrene insertion process. This new method is complementary to a previously reported pathway in which the C-4a/N-5 bond of the ring system is formed.

  DOI：

  10.3987/com-06-10879
• 作为产物：
  描述：

  4-氯-5-甲氧基-2-甲基-2,3-二氢哒嗪-3-酮 在 盐酸 、 四(三苯基膦)钯 、 二氮烯 、 sodium carbonate 、 sodium nitrite 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 5-azido-2-methyl-4-phenylpyridazin-3(2H)-one
  参考文献：
  名称：

  Thermolysis of 5-Azido-4-arylpyridazin-3(2H)-ones: An Efficient and Versatile Synthesis of Pyridazino[4,5-b]indoles

  摘要：

  5-Azido-4-arylpyridazin-3(2H)-ones, which are easily available from 4,5-dihalopyridazin-3(2H)-ones in few steps, were found to undergo in high yields a thermally induced cyclization into pyridazino[4,5-b]indole derivatives ("azacarbolinones") by formation of the N-5/C-5a bond via a nitrene insertion process. This new method is complementary to a previously reported pathway in which the C-4a/N-5 bond of the ring system is formed.

  DOI：

  10.3987/com-06-10879

文献信息

• Thermolysis of 5-Azido-4-arylpyridazin-3(2H)-ones: An Efficient and Versatile Synthesis of Pyridazino[4,5-b]indoles
  作者：Norbert Haider、Andrea Wobus

  DOI：10.3987/com-06-10879

  日期：——

  5-Azido-4-arylpyridazin-3(2H)-ones, which are easily available from 4,5-dihalopyridazin-3(2H)-ones in few steps, were found to undergo in high yields a thermally induced cyclization into pyridazino[4,5-b]indole derivatives ("azacarbolinones") by formation of the N-5/C-5a bond via a nitrene insertion process. This new method is complementary to a previously reported pathway in which the C-4a/N-5 bond of the ring system is formed.