2-(4-chlorophenyl)-6-methylquinazoline | 88737-71-7

• 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-(4-chlorophenyl)-6-methylquinazoline
• CAS: 88737-71-7
• 化学式: C₁₅H₁₁ClN₂
• 分子量: 254.719
• InChiKey: OAXQPTDIRDNCOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-Chloro-N-[1-dimethylamino-meth-(E)-ylidene]-N'-p-tolyl-benzamidine 在 PPA 作用下， 以75%的产率得到2-(4-chlorophenyl)-6-methylquinazoline
  参考文献：
  名称：

  New synthesis of quinazoline and benzoquinazoline derivatives

  摘要：

  DOI：

  10.1016/s0040-4039(00)88339-2

文献信息

• Accessing Polysubstituted Quinazolines via Nickel Catalyzed Acceptorless Dehydrogenative Coupling
  作者：Seuli Parua、Rina Sikari、Suman Sinha、Gargi Chakraborty、Rakesh Mondal、Nanda D. Paul

  DOI：10.1021/acs.joc.8b01479

  日期：2018.9.21

  easy to prepare nickel catalysts, containing tetraaza macrocyclic ligands (tetramethyltetraaza[14]annulene (MeTAA) or 6,15-dimethyl-8,17-diphenyltetraaza[14]annulene (MePhTAA)) are reported. A wide variety of substituted quinazolines were synthesized in moderate to high yields starting from cheap and easily available starting precursors. A few control reactions were performed to understand the mechanism

  通过2-氨基苄胺与苄醇的无受体脱氢偶联（路径A）和2-氨基苄基醇与苄腈的无受体脱氢偶联（路径B）来合成喹唑啉的两种对环境有益的方法，它们是由廉价的，富含地球的，易于制备的含四氮杂的镍催化剂催化的报道了大环配体（四甲基四氮杂[14]环烯（MeTAA）或6,15-二甲基-8,17-二苯基四氮杂[14]环烯（MePhTAA））。从廉价且容易获得的起始前体开始，以中等至高收率合成了多种取代的喹唑啉。进行了一些控制反应，以了解机理并建立催化反应的无受体脱氢性质。
• Access to 2-arylquinazolines <i>via</i> catabolism/reconstruction of amino acids with the insertion of dimethyl sulfoxide
  作者：Jin-Tian Ma、Li-Sheng Wang、Zhi Chai、Xin-Feng Chen、Bo-Cheng Tang、Xiang-Long Chen、Cai He、Yan-Dong Wu、An-Xin Wu

  DOI：10.1039/d1cc00623a

  日期：——

  Quinazoline skeletons are synthesized by amino acid catabolism/reconstruction combined with the insertion/cyclization of dimethyl sulfoxide for the first time. The amino acid acts as a carbon and nitrogen source through HI-mediated catabolism and is then reconstructed using aromatic amines and dimethyl sulfoxide (DMSO) as a one-carbon synthon. This protocol is of great significance for the further

  喹唑啉骨架是首次通过氨基酸分解代谢/重建结合二甲基亚砜的插入/环化合成。氨基酸通过 HI 介导的分解代谢充当碳和氮源，然后使用芳香胺和二甲基亚砜 (DMSO) 作为单碳合成子进行重建。该方案对进一步研究氨基酸转化具有重要意义。
• Dehydrogenative Synthesis of Quinolines, 2-Aminoquinolines, and Quinazolines Using Singlet Diradical Ni(II)-Catalysts
  作者：Gargi Chakraborty、Rina Sikari、Siuli Das、Rakesh Mondal、Suman Sinha、Seemika Banerjee、Nanda D. Paul

  DOI：10.1021/acs.joc.8b03070

  日期：2019.3.1

  Simple, straightforward, and atom economic methods for the synthesis of quinolines, 2-aminoquinolines, and quinazolines via biomimetic dehydrogenative condensation/coupling reactions, catalyzed by well-defined inexpensive and easy to prepare singlet diradical Ni(II)-catalysts featuring two antiferromagnetically coupled singlet diradical diamine type ligands are described. Various polysubstituted quinolines

  通过仿生脱氢缩合/偶合反应进行仿生脱氢缩合/偶合反应合成喹啉，2-氨基喹啉和喹唑啉的简单，直接和原子经济的方法，催化方法是定义明确的廉价且易于制备的具有两个反铁磁耦​​合的单重双自由基Ni（II）催化剂。描述了单线双自由基二胺型配体。各种多取代的喹啉，2-氨基喹啉和喹唑啉由不同的低成本且易于获得的起始原料以中等至良好的产率合成。进行了一些对照实验，以了解反应机理，结果表明镍和配位的二胺配体在醇的脱氢过程中以协同方式参与。
• A Novel Ruthenium-Catalyzed Dehydrogenative Synthesis of 2-Arylquinazolines from 2-Aminoaryl Methanols and Benzonitriles
  作者：Mengmeng Chen、Min Zhang、Biao Xiong、Zhenda Tan、Wan Lv、Huanfeng Jiang

  DOI：10.1021/ol503052s

  日期：2014.11.21

  By employing a commercially available Ru-3(CO)(12)/Xantphos/t-BuOK catalyst system, a novel and straightforward ruthenium-catalyzed dehydrogenative synthesis of 2-arylquinazolines has been demonstrated. A series of 2-aminoaryl methanols were efficiently converted in combination with different types of benzonitriles into various desired products in moderate to good yields upon isolation. The synthetic protocol proceeds with the advantages of operational simplicity, high atom efficiency, broad substrate scope, and no need for the use of less environmentally benign halogenated reagents, offering an important basis for accessing 2-arylquinazolines.