4-methyl-2-(thiophen-2-yl)quinazoline | 949876-98-6

• 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: 4-methyl-2-(thiophen-2-yl)quinazoline
• 英文别名: 4-Methyl-2-thiophen-2-ylquinazoline
• CAS: 949876-98-6
• 化学式: C₁₃H₁₀N₂S
• 分子量: 226.302
• InChiKey: HODGIZKSOCGVOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2'-(2-thienylmethyleneamino)acetophenone oxime 以 乙腈 为溶剂， 以73%的产率得到4-methyl-2-(thiophen-2-yl)quinazoline
  参考文献：
  名称：

  An efficient synthesis of quinazolines: a theoretical and experimental study on the photochemistry of oxime derivatives

  摘要：

  A new photochemical method for the preparation of quinazolines (2) through irradiation of [2-(methyleneamino)phenyl]methanone oximes (1) is reported. The photoreaction has been studied in depth by experimental, theoretical and photochemical methods. A six-electron electrocyclic ring closure mechanism, followed by water loss, is proposed and rationalized to explain the formation of quinazolines (2). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.082

文献信息

• Hydrogen peroxide-mediated synthesis of 2,4-substituted quinazolines <i>via</i> one-pot three-component reactions under metal-free conditions
  作者：Khang H. Trinh、Khang X. Nguyen、Phuc H. Pham、Tung T. Nguyen、Anh N. Q. Phan、Nam T. S. Phan

  DOI：10.1039/d0ra05040g

  日期：——

  An efficient metal-free synthesis of 2,4-substituted quinazolines via a hydrogen peroxide-mediated one-pot three-component reaction of 2-aminoaryl ketones, aldehydes, and ammonium acetate has been developed. The transformation proceeded readily under mild conditions in the presence of commercially available hydrogen peroxide. The significant advantages of this approach are (1) the readily available

  2,4-取代喹唑啉的高效无金属合成已经开发了过氧化氢介导的 2-氨基芳基酮、醛和乙酸铵的一锅三组分反应。在市售过氧化氢存在的温和条件下，转化很容易进行。这种方法的显着优点是（1）容易获得的原子效率和绿色过氧化氢作为氧化剂；(2)不需要过渡金属催化剂；(3) 反应条件温和；(4)基材范围广。据我们所知，利用过氧化氢作为一种原子效率高的绿色氧化剂来合成 2,4-取代的喹唑啉，以前没有文献报道过。该方法是对先前合成 2,4-取代喹唑啉的协议的补充。
• n-Bu₄NI-catalyzed selective dual amination of sp³ C–H bonds: oxidative domino synthesis of imidazo[1,5-c]quinazolines on a gram-scale
  作者：Dan Zhao、Teng Wang、Qi Shen、Jian-Xin Li

  DOI：10.1039/c4cc01444h

  日期：——

  An n-Bu4NI catalyzed domino reaction that involves selective dual amination of sp(3) C-H bonds has been developed. The protocol affords a facile and efficient approach to the synthesis of imidazo[1,5-c]quinazolines under mild conditions.

  已开发出n-Bu4NI催化的多米诺骨牌反应，该反应涉及sp（3）CH键的选择性双重胺化。该方案为在温和条件下合成咪唑并[1,5-c]喹唑啉提供了一种简便而有效的方法。
• Vinylene carbonate: beyond the ethyne surrogate in rhodium-catalyzed annulation with amidines toward 4-methylquinazolines
  作者：Chang Wang、Xiaodong Fan、Fan Chen、Peng-Cheng Qian、Jiang Cheng

  DOI：10.1039/d1cc00882j

  日期：——

  Vinylene carbonate: acetylation reagent rather than ethyne surrogate in rhodium-catalyzed annulation with amidines toward 4-methylquinazolines.

  乙烯基碳酸酯：在铑催化的与酰胺合成4-甲基喹唑啉的环化反应中，作为乙炔代用试剂的乙酰化试剂。
• Fe–FeO_<i>x</i> nanoparticles encapsulated in N-doped carbon material: a facile catalyst for selective synthesis of quinazolines from alcohols in water
  作者：Fei Wang、Fuying Zhu、Enxiang Ren、Qiang Zhang、Guo-Ping Lu、Yamei Lin

  DOI：10.1039/d2cy01562e

  日期：——

  and green synthetic strategies for N-heterocycle synthesis has always been a research hotspot in organic synthesis. A facile one-pot iron-catalyzed synthesis of quinazolines from alcohols in water has been disclosed for the first time, in which a N-doped carbon encapsulated Fe–FeOx material (Fe–FeOx@NC) is applied as a catalyst, and various quinazolines (25 examples, 62–99%) are synthesized. The iron

  开发高效、绿色的N-杂环合成策略一直是有机合成领域的研究热点。首次公开了一种简便的铁催化水中醇合成喹唑啉的方法，其中将 N 掺杂碳包覆的 Fe-FeO x材料（Fe-FeO x @NC）用作催化剂，并合成了各种喹唑啉（25 个实例，62-99%）。Fe-FeO x @NC中被氮掺杂碳层包裹的铁纳米颗粒具有很强的抗毒能力，是该反应具有高性能的主要原因。该协议提供了几个优点，包括使用空气作为氧化剂、水作为溶剂、可回收铁作为催化剂以及高原子和步骤经济性。
• Photocatalytic synthesis of 2,4‐substituted quinazolines via a one‐pot, three‐component reaction under catalyst‐free conditions
  作者：Zongbo Xie、Xuehua Chen、Guofang Jiang、Qianwen Fan、Hong Yang、Zhanggao Le

  DOI：10.1002/jhet.4810

  日期：——

  A novel, catalyst-free photoinduced synthesis of 2,4-substituted quinazoline using 2-amino-aryl ketone, an aldehyde, and ammonium acetate was developed. A series of 2,4-substituted quinazoline compounds were obtained via irradiating the reactants with a light-emitting diode light (18 W) at room temperature. The broad substrate range and excellent gram-scale experimental results demonstrate the versatility

  使用 2-氨基芳基酮、醛和乙酸铵开发了一种新型、无催化剂的光诱导合成 2,4-取代喹唑啉。在室温下用发光二极管光(18W)照射反应物得到一系列2,4-取代喹唑啉化合物。广泛的底物范围和出色的克级实验结果证明了该反应的多功能性。据我们所知，以醋酸铵为氮源在光催化下合成2,4-取代喹唑啉的报道尚未见报道。该方法利用可见光氧化来消除反应中氧化剂的使用，是对以前方法的补充。