6-(1H-1,2,3-benzotriazol-1-yl)-5-methyl-2-(4-methylphenyl)-3-oxo-2,3-dihydropyridazine-4-carbonitrile | 255375-28-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 6-(1H-1,2,3-benzotriazol-1-yl)-5-methyl-2-(4-methylphenyl)-3-oxo-2,3-dihydropyridazine-4-carbonitrile
• 英文别名: 3-(benzotriazol-1-yl)-1,6-dihydro-4-methyl-6-oxo-1-p-methylphenylpyridazine-5-carbonitrile；6-(Benzotriazol-1-yl)-5-methyl-2-(4-methylphenyl)-3-oxopyridazine-4-carbonitrile
• CAS: 255375-28-1
• 化学式: C₁₉H₁₄N₆O
• 分子量: 342.36
• InChiKey: BFBUEBBGTMAKDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  87.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-(1H-1,2,3-benzotriazol-1-yl)-5-methyl-2-(4-methylphenyl)-3-oxo-2,3-dihydropyridazine-4-carbonitrile 在 哌啶 、 sulfur 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.03h， 以88%的产率得到7-amino-4-(1H-1,2,3-benzotriazol-1-yl)-2-(4-methylphenyl)thieno[3,4-d]pyridazin-1(2H)-one
  参考文献：
  名称：

  A Microwave Assisted Diazo Coupling Reaction: The Synthesis of Alkylazines and Thienopyridazines

  摘要：

  Heating diazoaminobenzene with active methylene compounds 1-3 in microwave oven in acetic acid, in the presence of hydrochloric acid, afforded the corresponding arylhydrazones 5-7. These reaction products were condensed with ethyl cyanoacetate in a domestic microwave oven after 1-2 minutes heating to yield the pyridazinones 8-12. Compounds 8c and 12 reacted with sulfur in basic DMF solution, in microwave oven using MORE technology to yield the thienopyridazinone 14 and 16 respectively. While 17 was produced when 8b was treated like wise with sulfur and DMF in the presence of piperidine. Compounds 16 coupled with aromatic diazonium salts to yield arylazo derivatives 21a-c.

  DOI：

  10.1080/10426500500536457
• 作为产物：
  描述：

  1-(1H-1,2,3-苯并噻唑-1-基)乙酮 在 乙酸铵 、 盐酸 、 溶剂黄146 作用下， 反应 0.06h， 生成 6-(1H-1,2,3-benzotriazol-1-yl)-5-methyl-2-(4-methylphenyl)-3-oxo-2,3-dihydropyridazine-4-carbonitrile
  参考文献：
  名称：

  A Microwave Assisted Diazo Coupling Reaction: The Synthesis of Alkylazines and Thienopyridazines

  摘要：

  Heating diazoaminobenzene with active methylene compounds 1-3 in microwave oven in acetic acid, in the presence of hydrochloric acid, afforded the corresponding arylhydrazones 5-7. These reaction products were condensed with ethyl cyanoacetate in a domestic microwave oven after 1-2 minutes heating to yield the pyridazinones 8-12. Compounds 8c and 12 reacted with sulfur in basic DMF solution, in microwave oven using MORE technology to yield the thienopyridazinone 14 and 16 respectively. While 17 was produced when 8b was treated like wise with sulfur and DMF in the presence of piperidine. Compounds 16 coupled with aromatic diazonium salts to yield arylazo derivatives 21a-c.

  DOI：

  10.1080/10426500500536457

文献信息

• Al-Naggar, Abdul Aziz; Abdel-Khalik, Mervat Mohammed; Elnagdi, Mohammed Hilmy, Journal of Chemical Research, Miniprint, 1999, # 11, p. 2801 - 2810
  作者：Al-Naggar, Abdul Aziz、Abdel-Khalik, Mervat Mohammed、Elnagdi, Mohammed Hilmy

  DOI：——

  日期：——
• A Microwave Assisted Diazo Coupling Reaction: The Synthesis of Alkylazines and Thienopyridazines
  作者：Saleh Al-Mousawi、Abdel-Zaher Elassar、Morsy Ahmed El-Apasery

  DOI：10.1080/10426500500536457

  日期：2006.8.1

  Heating diazoaminobenzene with active methylene compounds 1-3 in microwave oven in acetic acid, in the presence of hydrochloric acid, afforded the corresponding arylhydrazones 5-7. These reaction products were condensed with ethyl cyanoacetate in a domestic microwave oven after 1-2 minutes heating to yield the pyridazinones 8-12. Compounds 8c and 12 reacted with sulfur in basic DMF solution, in microwave oven using MORE technology to yield the thienopyridazinone 14 and 16 respectively. While 17 was produced when 8b was treated like wise with sulfur and DMF in the presence of piperidine. Compounds 16 coupled with aromatic diazonium salts to yield arylazo derivatives 21a-c.