6-methyl-2-phenylquinazolin-4-amine

• 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: 6-methyl-2-phenylquinazolin-4-amine
• 英文别名: 6-Methyl-4-amino-2-phenylquinazoline
• 化学式: C₁₅H₁₃N₃
• mdl: MFCD20939801
• 分子量: 235.288
• InChiKey: BTBPATYJCRYQAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.066
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯并-p-甲苯胺 在 五氯化磷 、 四氯化钛 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 6-methyl-2-phenylquinazolin-4-amine
  参考文献：
  名称：

  Synthesis and Basicity of 4-Amino-2-phenylquinazolines

  摘要：

  A new group of 6- and 7-substituted compounds of 4-amino-2-phenylquinazoline were synthesized by reaction of N-arylbenzimidoyl chlorides with cyanamide in the presence of TiCl4. The products were identified by spectroscopic methods, their dissociation constants were determined and are discussed.

  DOI：

  10.1007/s007060070067

文献信息

• Expeditious Synthesis of 2-Phenylquinazolin-4-amines via a Fe/Cu Relay-Catalyzed Domino Strategy
  作者：Feng-Cheng Jia、Zhi-Wen Zhou、Cheng Xu、Qun Cai、Deng-Kui Li、An-Xin Wu

  DOI：10.1021/acs.orglett.5b02020

  日期：2015.9.4

  efficient Fe/Cu relay-catalyzed domino protocol has been developed for the synthesis of 2-phenylquinazolin-4-amines from commercially available ortho-halogenated benzonitriles, aldehydes, and sodium azide. This elegant domino process involved consecutive iron-mediated [3 + 2] cycloaddition, copper-catalyzed SNAr, reduction, cyclization, oxidation, and copper-catalyzed denitrogenation sequences. The formed structure

  已经开发了一种高效的Fe / Cu中继催化多米诺协议，用于从可商购的邻卤代苄腈，醛和叠氮化钠合成2-苯基喹唑啉-4-胺。这种优美的多米诺骨牌工艺涉及连续的铁介导的[3 + 2]环加成，铜催化的S N Ar，还原，环化，氧化和铜催化的脱氮序列。形成的结构是药物和生物活性分子中的特权核心。
• A Highly Efficient Copper-Catalyzed Three-Component Synthesis of 4-Aminoquinazolines
  作者：Lei Yang、Honghua Luo、Yan Sun、Zhenyu Shi、Kaidong Ni、Fei Li、Dongyin Chen

  DOI：10.1055/s-0036-1588727

  日期：2017.6

  in 50–90% yield. A highly efficient copper-catalyzed one-pot protocol is developed for the synthesis of 4-aminoquinazolines from easily available 2-iodo- or 2-bromobenzimidamides, aldehydes, and sodium azide. This one-pot approach proceeds via consecutive copper-catalyzed SNAr substitution, reduction, cyclization, oxidation and tautomerization. The corresponding target products (26 examples) are obtained

  摘要 开发了一种高效的铜催化一锅法，用于从易于获得的2-碘或2-溴代苯甲酰胺，醛和叠氮化钠合成4-氨基喹唑啉。这种一锅法是通过连续的铜催化的S N Ar取代，还原，环化，氧化和互变异构进行的。以50–90％的收率获得了相应的目标产品（26个实例）。 开发了一种高效的铜催化一锅法，用于从易于获得的2-碘或2-溴代苯甲酰胺，醛和叠氮化钠合成4-氨基喹唑啉。这种一锅法是通过连续的铜催化的S N Ar取代，还原，环化，氧化和互变异构进行的。以50–90％的收率获得了相应的目标产品（26个实例）。
• Efficient synthesis of 2-arylquinazolin-4-amines <i>via</i> a copper-catalyzed diazidation and ring expansion cascade of 2-arylindoles
  作者：Meng-Meng Xu、Wen-Bin Cao、Xiao-Ping Xu、Shun-Jun Ji

  DOI：10.1039/c8cc07721e

  日期：——

  Copper-catalyzed synthesis of 2-arylquinazolin-4-amines from readily available 2-arylindoles and TMSN3 has been developed. The mechanism study shows that the domino reaction may involve a free radical diazidation, denitrogenation, intramolecular cyclization and ring expansion sequence.

  已经开发出铜催化的从容易获得的2-芳基吲哚和TMSN 3合成2-芳基喹唑啉-4-胺的方法。机理研究表明，多米诺反应可能涉及自由基的叠氮化，脱氮，分子内环化和环扩环。
• Simple efficient synthesis of 4-aminoquinazoline via amidine of N-arylamidoxime
  作者：Sachin S. Patil、Pravin C. Mhaske、Sachin V. Patil、Vivek D. Bobade

  DOI：10.1002/jhet.572

  日期：2011.5

  Preparation of 4‐amino‐2‐aryl quinazolines by reduction of N‐(2‐cyanoaryl) amidoximes via amidines using SnCl2 in ethanol. J. Heterocyclic Chem., (2011).

  使用乙醇中的SnCl 2通过via还原N-（2-氰基芳基）氨基肟来制备4-氨基-2-芳基喹唑啉。J.杂环化​​学。（2011）。
• Efficient Copper-Catalyzed Synthesis of 4-Aminoquinazoline and 2,4-Diaminoquinazoline Derivatives
  作者：Hua Fu、Renzhong Qiao、Xiaobo Yang、Hongxia Liu、Yuyang Jiang、Yufen Zhao

  DOI：10.1055/s-0029-1218530

  日期：2010.1

  We have developed an efficient copper-catalyzed method for the synthesis of 4-aminoquinazoline and 2,4-diaminoquinazoline derivatives via reactions of substituted 2-bromobenzonitriles with amidines or guanidine, and the method is of economical and practical advantage.