(4-diacetamido-6-methyl-cinnolin-3-yl)-p-tolyl-methanone | 256639-42-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-diacetamido-6-methyl-cinnolin-3-yl)-p-tolyl-methanone
• 英文别名: N-acetyl-N-[6-methyl-3-(4-methylbenzoyl)cinnolin-4-yl]acetamide
• CAS: 256639-42-6
• 化学式: C₂₁H₁₉N₃O₃
• 分子量: 361.4
• InChiKey: RGJQYQORUPGGDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  80.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-diacetamido-6-methyl-cinnolin-3-yl)-p-tolyl-methanone 在 ammonium acetate 、 氨 作用下， 反应 3.0h， 以35%的产率得到2,9-dimethyl-4-(p-tolyl)-pyrimido[5,4-c]cinnoline
  参考文献：
  名称：

  On the Chemistry of Cinnoline I. Synthesis and Reactions of (4-Amino-cinnolin-3-yl)-p-tolyl-methanones

  摘要：

  The synthesis of a series of (4-Amino-cinnolin-3-yl)-p-tolyl-methanones from aryl-hydrazonomalononitrile in a one step procedure is reported. The (4-amino-cinnolin-3-yl)-p-tolyl- methanones could be annelated to the corresponding 1,2-dihydro-4-(p-tolyl)-2-oxopyrido[3,2-c]cinnoline derivatives via (4-acetamido-cinnolin-3-yl)-p-tolyl-methanones. Treatment of 1,2-dihydro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline-2-one with POCl3 and P2S5 gave 2-chloro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline. and 1,2-dihydro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline-2-thione. Treatment of the ketone with malononitrile afforded 2-amino-3-cyano-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline. Using these ketones, a facile and convenient route towards substituted pyrimidino[5,4-c]-cinnolines was developed. Chemical and spectroscopic evidences for the structures of the new compounds are presented.

  DOI：

  10.1007/pl00010201
• 作为产物：
  描述：

  2-[2-(4-methylphenyl)hydrazono]malononitrile 在 三氯化铝 作用下， 反应 5.0h， 生成 (4-diacetamido-6-methyl-cinnolin-3-yl)-p-tolyl-methanone
  参考文献：
  名称：

  On the Chemistry of Cinnoline I. Synthesis and Reactions of (4-Amino-cinnolin-3-yl)-p-tolyl-methanones

  摘要：

  The synthesis of a series of (4-Amino-cinnolin-3-yl)-p-tolyl-methanones from aryl-hydrazonomalononitrile in a one step procedure is reported. The (4-amino-cinnolin-3-yl)-p-tolyl- methanones could be annelated to the corresponding 1,2-dihydro-4-(p-tolyl)-2-oxopyrido[3,2-c]cinnoline derivatives via (4-acetamido-cinnolin-3-yl)-p-tolyl-methanones. Treatment of 1,2-dihydro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline-2-one with POCl3 and P2S5 gave 2-chloro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline. and 1,2-dihydro-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline-2-thione. Treatment of the ketone with malononitrile afforded 2-amino-3-cyano-9-methyl-4-(p-tolyl)-pyrido[3,2-c]cinnoline. Using these ketones, a facile and convenient route towards substituted pyrimidino[5,4-c]-cinnolines was developed. Chemical and spectroscopic evidences for the structures of the new compounds are presented.

  DOI：

  10.1007/pl00010201