6-chloro-2-(4-chlorophenyl)quinazoline | 1353000-34-6

• 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-chloro-2-(4-chlorophenyl)quinazoline
• 英文别名: 6-chloro-2-(p-chlorophenyl)quinazoline
• CAS: 1353000-34-6
• 化学式: C₁₄H₈Cl₂N₂
• 分子量: 275.137
• InChiKey: FNZTTYWFMRSGPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  在 三乙烯二胺 、 阻聚剂701 、 氧气 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 10.0h， 生成 6-chloro-2-(4-chlorophenyl)quinazoline
  参考文献：
  名称：

  CuCl / DABCO / 4-HO-TEMPO催化2-取代的喹唑啉和4 H -3,1-Benzoxazines的好氧氧化合成

  摘要：

  Cu / N-配体/ TEMPO催化体系首先被用于杂环的好氧氧化合成。如所证明的，通过使用CuCl / DABCO / 4-HO-TEMPO分别由醛与2-氨基苄胺和2-氨基苄醇的一锅反应有效地合成了2-取代的喹唑啉和4 H -3,1-苯并恶嗪。作为催化剂，氧气作为末端氧化剂。

  DOI：

  10.1021/jo2020399

文献信息

• Synthesis of 2-substituted quinazolines by CsOH-mediated direct aerobic oxidative cyclocondensation of 2-aminoarylmethanols with nitriles in air
  作者：Song Yao、Kaijing Zhou、Jiabing Wang、Hongen Cao、Lei Yu、Jianzhang Wu、Peihong Qiu、Qing Xu

  DOI：10.1039/c7gc00977a

  日期：——

  atom-efficient synthesis of 2-substituted quinazolines is developed by a CsOH-mediated direct aerobic oxidative reaction of the readily available and stable 2-aminoarylmethanols and nitriles. Effectively working as the promoter in the alcohol oxidation, nitrile hydration, and cyclocondensation steps, CsOH is the best base for the reaction. A similar method can also be extended to the synthesis of substituted

  通过使用空气作为优越的氧化剂，通过CsOH介导的易获得且稳定的2-氨基芳基甲醇和腈的直接好氧氧化反应，可以开发出原子高效的2-取代的喹唑啉合成方法。CsOH有效地用作醇氧化，腈水合和环缩合步骤中的促进剂，是反应的最佳碱。类似的方法也可以扩展到从甲基酮而不是腈开始的取代喹啉的合成。
• Nickel-Catalyzed [4 + 2] Annulation of Nitriles and Benzylamines by C–H/N–H Activation
  作者：Rina Sikari、Gargi Chakraborty、Amit Kumar Guin、Nanda D. Paul

  DOI：10.1021/acs.joc.0c02069

  日期：2021.1.1

  Nickel-catalyzed [4 + 2] annulation of benzylamines and nitriles via C–H/N–H bond activation, providing straightforward atom-economic access to a wide variety of multisubstituted quinazolines, is reported. Mechanistic investigation revealed that the in situ formed amidines from the coupling of benzylamines and nitriles direct the nickel catalyst to activate the ortho-C–H bond of the phenyl ring of

  据报道，镍的苄基胺和腈的[4 + 2]环合反应通过C–H / N–H键活化作用，可直接经济地获得各种多取代的喹唑啉。机理研究表明，由苄胺和腈偶联而形成的am直接引导镍催化剂活化苄胺苯环的邻-C-H键。
• Sustainable Synthesis of Quinazoline and 2-Aminoquinoline via Dehydrogenative Coupling of 2-Aminobenzyl Alcohol and Nitrile Catalyzed by Phosphine-Free Manganese Pincer Complex
  作者：Kalicharan Das、Avijit Mondal、Debjyoti Pal、Dipankar Srimani

  DOI：10.1021/acs.orglett.9b00939

  日期：2019.5.3

  A sustainable synthesis of quinazoline and 2-aminoquinoline via acceptorless dehydrogenative annulation is presented. The reaction is catalyzed by earth-abundant well-defined manganese complexes bearing NNS ligands. Furthermore, a one-pot synthetic strategy for the synthesis of 2-alkylaminoquinolines through sequential dehydrogenative annulation and N-alkylation reaction has also been demonstrated

  提出了通过无受体脱氢环化法可持续合成喹唑啉和2-氨基喹啉的方法。该反应由富含NNS配体的地球上定义明确的锰配合物催化。此外，还证明了通过顺序脱氢环化和N-烷基化反应合成2-烷基氨基喹啉的一锅合成策略。
• NNN pincer Ru(II)-catalyzed dehydrogenative coupling of 2-aminoarylmethanols with nitriles for the construction of quinazolines
  作者：Xiao-Min Wan、Zi-Lin Liu、Wan-Qing Liu、Xiao-Niu Cao、Xinju Zhu、Xue-Mei Zhao、Bing Song、Xin-Qi Hao、Guoji Liu

  DOI：10.1016/j.tet.2019.03.046

  日期：2019.5

  Ru(II)-catalyzed preparation of quinazolines via acceptorless dehydrogenative strategy has been developed. Under the optimized conditions, a broad range of substituted o-aminobenzyl alcohols and (hetero)aryl or alkyl nitriles were well tolerated to afford various 2-substituted quinazolines in high yields. Subsequently, a set of control experiments have been performed to elucidate the reaction mechanism,

  通过无受体脱氢策略开发了一种有效的NNN钳入Ru（II）催化的喹唑啉制备方法。在优化的条件下，很好地耐受了广泛范围的取代的邻氨基苄醇和（杂）芳基或烷基腈，从而以高收率提供了各种2-取代的喹唑啉。随后，进行了一系列对照实验以阐明反应机理，该机理经历了醇氧化，腈水合和环缩合步骤。当前的协议具有几个优点，例如环境友好，操作简便，底物范围广（与脂族腈兼容，产率高达87％）和反应时间短（大部分在2小时之内）。
• 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.