2-(2-bromophenyl)-3-(phenylamino)quinazolin-4(3H)-one | 1452386-76-3

• 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: 2-(2-bromophenyl)-3-(phenylamino)quinazolin-4(3H)-one
• 英文别名: 3-Anilino-2-(2-bromophenyl)quinazolin-4-one
• CAS: 1452386-76-3
• 化学式: C₂₀H₁₄BrN₃O
• 分子量: 392.255
• InChiKey: SOYPIQVVKMWPFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-bromophenyl)-3-(phenylamino)quinazolin-4(3H)-one 在 caesium carbonate 、 L-脯氨酸 、 copper(l) chloride 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以88%的产率得到5-phenylindazolo[3,2-b]quinazolin-7(5H)-one
  参考文献：
  名称：

  Copper-catalyzed intramolecular C–N bond formation reaction of 3-amino-2-(2-bromophenyl)dihydroquinazolinones: synthesis of indazolo[3,2-b]quinazolinones

  摘要：

  A copper-catalyzed intramolecular C-N bond formation reaction of 3-amino-2-(2-bromophenyl)dihydroquinazolinones has been developed for the synthesis of indazolo[3,2-b]quinazolinones in moderate to good yields. The structure of the newly synthesized indazolo[3,2-b]quinazolinones was unambiguously confirmed by X-ray single-crystal diffraction analysis. Moreover, a possible mechanism for the formation of indazolo[3,2-b]quinazolinones is discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.012
• 作为产物：
  描述：

  2-(2-bromophenyl)-3-(phenylamino)-2,3-dihydroquinazolin-4(1H)-one 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以72%的产率得到2-(2-bromophenyl)-3-(phenylamino)quinazolin-4(3H)-one
  参考文献：
  名称：

  Copper-catalyzed intramolecular C–N bond formation reaction of 3-amino-2-(2-bromophenyl)dihydroquinazolinones: synthesis of indazolo[3,2-b]quinazolinones

  摘要：

  A copper-catalyzed intramolecular C-N bond formation reaction of 3-amino-2-(2-bromophenyl)dihydroquinazolinones has been developed for the synthesis of indazolo[3,2-b]quinazolinones in moderate to good yields. The structure of the newly synthesized indazolo[3,2-b]quinazolinones was unambiguously confirmed by X-ray single-crystal diffraction analysis. Moreover, a possible mechanism for the formation of indazolo[3,2-b]quinazolinones is discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.012

文献信息

• A Practical, Ligand-Free, Palladium-Catalyzed Isocyanide Insertion Reaction for the Construction of Novel Ring-Fused Quinazolinones
  作者：Chun Cai、Fei Ji、Mei-fang Lv、Wen-bin Yi

  DOI：10.1055/s-0033-1338936

  日期：——

  anhydrides, phenylhydrazines and 2-bromobenzaldehyde catalyzed by p-toluenesulfonic acid in one pot. This novel protocol may be applicable for the synthesis of other important ring-fused heterocyclic compounds. A high-yielding, ligand-free, palladium-catalyzed isocyanide insertion reaction for the synthesis of phthalazino[1,2-b]quinazolinones from the readily obtainable quinazolinones has been developed

  摘要 已经开发出一种高产率，无配体，钯催化的异氰酸酯插入反应，用于由容易获得的喹唑啉酮合成邻苯并[1,2- b ]喹唑啉酮。易于处理且成本相对较低的乙酸钯（II）用作催化剂，无需额外的配体。喹唑啉酮的制备涉及在一锅中对甲苯磺酸，苯肼和2-溴苯甲醛由对甲苯磺酸催化的级联反应。这种新颖的协议可能适用于其他重要的环稠合杂环化合物的合成。 已经开发出一种高产率，无配体，钯催化的异氰酸酯插入反应，用于由容易获得的喹唑啉酮合成邻苯并[1,2- b ]喹唑啉酮。易于处理且成本相对较低的乙酸钯（II）用作催化剂，无需额外的配体。喹唑啉酮的制备涉及在一锅中对甲苯磺酸，苯肼和2-溴苯甲醛由对甲苯磺酸催化的级联反应。这种新颖的协议可能适用于其他重要的环稠合杂环化合物的合成。
• Pd-Catalyzed Intramolecular Aerobic Oxidative C–H Amination of 2-Aryl-3-(arylamino)quinazolinones: Synthesis of Fluorescent Indazolo[3,2-<i>b</i>]quinazolinones
  作者：Weiguang Yang、Jiuxi Chen、Xiaobo Huang、Jinchang Ding、Miaochang Liu、Huayue Wu

  DOI：10.1021/ol5026553

  日期：2014.10.17

  A palladium-catalyzed intramolecular aerobic oxidative C-H amination of 2-aryl-3-(arylamino)quinazolinones has been developed, providing a variety of substituted indazolo[3,2-b]quinazolinone derivatives in moderate to excellent yields. Preliminary mechanistic studies suggested that a palladacycle dimer could be the key intermediate, which underwent a cascade "rollover" cyclometalation and C-H amination sequence. Furthermore, the potential utility of these products has been demonstrated as a new class of blue fluorophores for fluorescent materials.