N-(2,3-dichlorophenyl)-6-nitroquinazolin-4-amine | 1233868-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-(2,3-dichlorophenyl)-6-nitroquinazolin-4-amine
• 英文别名: N-(2,3-dichlorophenyl)-6-nitro-4-Quinazolinamine
• CAS: 1233868-85-3
• 化学式: C₁₄H₈Cl₂N₄O₂
• 分子量: 335.149
• InChiKey: DSRSZUJGLLIQMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N'-(2-氰基-4-硝基苯基)-N,N-二甲基亚胺甲酰胺 、 2,3-二氯苯胺 在 溶剂黄146 作用下， 反应 1.5h， 以60%的产率得到N-(2,3-dichlorophenyl)-6-nitroquinazolin-4-amine
  参考文献：
  名称：

  Microwave-accelerated Dimroth rearrangement for the synthesis of 4-anilino-6-nitroquinazolines. Application to an efficient synthesis of a microtubule destabilizing agent

  摘要：

  A useful and rapid access to 4-anilino-6-nitroquinazolines was investigated in a multi-gram scale via microwave-accelerated condensation and Dimroth rearrangement of the starting anilines with imines obtained by reaction of anthranilonitriles with formamide dimethylacetal. A novel short and efficient route to AZiXa (TM) (EPi28495, MPC-6827), a microtubule destabilizing agent and apoptosis inducer, was performed with success demonstrating that well controlled parameters offer comfortable using of microwave technology with safe and environmental benefits. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.066

文献信息

• Microwave-accelerated Dimroth rearrangement for the synthesis of 4-anilino-6-nitroquinazolines. Application to an efficient synthesis of a microtubule destabilizing agent
  作者：Alicia Foucourt、Carole Dubouilh-Benard、Elizabeth Chosson、Cécile Corbière、Catherine Buquet、Mauro Iannelli、Bertrand Leblond、Francis Marsais、Thierry Besson

  DOI：10.1016/j.tet.2010.04.066

  日期：2010.6

  A useful and rapid access to 4-anilino-6-nitroquinazolines was investigated in a multi-gram scale via microwave-accelerated condensation and Dimroth rearrangement of the starting anilines with imines obtained by reaction of anthranilonitriles with formamide dimethylacetal. A novel short and efficient route to AZiXa (TM) (EPi28495, MPC-6827), a microtubule destabilizing agent and apoptosis inducer, was performed with success demonstrating that well controlled parameters offer comfortable using of microwave technology with safe and environmental benefits. (C) 2010 Elsevier Ltd. All rights reserved.