2-(thiophen-3-yl)quinazolin-4(3H)-one | 923800-74-2

• 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-(thiophen-3-yl)quinazolin-4(3H)-one
• 英文别名: 2-thien-3-ylquinazolin-4(3H)-one；2-thiophen-3-yl-3H-quinazolin-4-one
• CAS: 923800-74-2
• 化学式: C₁₂H₈N₂OS
• mdl: MFCD08444288
• 分子量: 228.274
• InChiKey: WQPHUKPKGIBCBO-UHFFFAOYSA-N

物化性质

• 沸点：
  411.5±37.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(thiophen-3-yl)quinazolin-4(3H)-one 在 劳森试剂 作用下， 以 1,4-二氧六环 为溶剂， 以80.3%的产率得到2-(thiophen-3-yl)-3H-quinazoline-4-thione
  参考文献：
  名称：

  2-Alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides: synthesis, molecular docking, antimicrobial and anticancer properties

  摘要：

  In this study, a series of novel 2-alkyl(aryl)-quinazolin-4(3H)-thiones, 2-R-(quinazolin-4(3H)-ylthio)carboxylic acids and amides were synthesized and evaluated for antimicrobial and anticancer activities. Their structure was confirmed by elemental analysis and spectral data (FT-IR, LC-MS, H-1-NMR). Antimicrobial activity was tested in vitro against Staphylococcus aureus, Enterococcus faecalis, Enterobacter aerogenes, Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumonia, Candida albicans and NCI in vitro preliminary anticancer activity against nine different cancer types. The most active antibacterial and antifungal compounds were: 2.1, 2.2 and 2.4. The introduction of the carboxylic acid or amide residue into the fourth position of quinazolin-4(3H)-thione resulted in the absence of antimicrobial activity. Substance 3.8 inhibited renal cancer UO-31 line and 2.18 - leukemia CCRF-CEM. The results of in silico molecular docking for DHFR and CK2 kinase had no correlation with in vitro properties, proposing the presence of other biological activity pathways.

  DOI：

  10.3109/14756366.2015.1018243
• 作为产物：
  描述：

  2-异硫氰基苯甲酸甲酯 在 吡啶 、 copper(I) 2-hydroxy-3-methylbenzoate 、 氨 、 sodium hydride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲苯 为溶剂， -34.0~100.0 ℃ 、200.0 kPa 条件下， 反应 3.17h， 生成 2-(thiophen-3-yl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Conversion of 2-Thioxo-2,3-dihydroquinazolin-4(1H)-ones to N(3)-Unsubstituted 2-(Het)Arylquinazolin-4(3H)-ones by Copper-Mediated Pd-Catalysed Cross-Coupling Reactions

  摘要：

  With the purpose of searching for new heterocyclic building blocks, a new method to access N(3)-unsubstituted 2-(het)arylquinazolin-4(3H)-ones from 2-thioxo-2,3-dihydroquinazolin-4(1H)-one derivatives was developed. The synthetic protocol was based on the copper-mediated palladium-catalysed cross-coupling reactions of 2-thioxo-2,3-dihydroquinazolin-4(1H)-ones with (het)arylstannanes or their S-benzylated derivatives with (het)arylboronic acids, using CuBr center dot Me2S and CuMeSal as promoters, respectively. A similar transformation was applied for the preparation of 2-aryl[ 1]benzothieno[3,2-d]pyrimidin-4(3H)-ones.

  DOI：

  10.3987/com-15-s(t)12

文献信息

• Palladium(II) N^O Chelating Complexes Catalyzed One-Pot Approach for Synthesis of Quinazolin-4(3<i>H</i>)-ones via Acceptorless Dehydrogenative Coupling of Benzyl Alcohols and 2-Aminobenzamide
  作者：Sundarraman Balaji、Gunasekaran Balamurugan、Rengan Ramesh、David Semeril

  DOI：10.1021/acs.organomet.0c00814

  日期：2021.3.22

  A convenient protocol for the one-pot synthesis of quinazolin-4(3H)-ones using palladium(II) complexes via dehydrogenative coupling of readily available benzyl alcohols and 2-aminobenzamide has been described. New structurally related Pd(II) N^O chelating complexes of general configuration [Pd(L)Cl(PPh3)] (where L = dimethylamino benzoylhydrazone ligands) have been designed and synthesized. The formation

  已经描述了一种方便的方案，该方案通过容易获得的苄醇和2-氨基苯甲酰胺的脱氢偶联使用钯（II）配合物一锅合成喹唑啉-4（3 H）-酮。新型[Pd（L）Cl（PPh 3）与结构相关的Pd（II）N ^ O螯合物）]（其中L =二甲基氨基苯甲酰hydr配体）已设计并合成。络合物的形成已通过分析和光谱方法（FT-IR，NMR，HR-MS）得到认可。通过单晶X射线衍射研究证实了钯（II）离子周围存在正方形平面的几何形状。在有氧条件下，使用1.0 mol％的催化剂负载量，可以从各种各样的苄醇中成功地成功获得各种各样的取代的喹唑啉酮类化合物，产率高至优异。此外，对照实验表明，脱氢偶联反应首先涉及醛中间体的形成，然后涉及环状氨基中间体的形成。
• Oxidative synthesis of quinazolinones and benzothiadiazine 1,1-dioxides from 2-aminobenzamide and 2-aminobenzenesulfonamide with benzyl alcohols and aldehydes
  作者：Muhammad Sharif、Julita Opalach、Peter Langer、Matthias Beller、Xiao-Feng Wu

  DOI：10.1039/c3ra45765f

  日期：——

  An interesting procedure for the zinc-catalyzed oxidative transformation of ready available 2-aminobenzamide, 2-aminobenzenesulfonamide with benzyl alcohols has been developed. Various quinazolinones and benzothiadiazine 1,1-dioxides were prepared in moderate to good yields under identical conditions. The reactions of both aromatic aldehydes and aliphatic aldehydes with 2-aminobenzamide under catalyst free conditions were described as well. In water media, the products were formed in good yields.

  开发了一种有趣的过程，用于锌催化氧化转化易于获得的2-氨基苯甲酰胺和2-氨基苯磺酰胺与苄醇。在相同条件下，制备了各种喹唉酮和苯并噻二嗪1,1-二氧化物，产率中等至良好。此外，还描述了在无催化剂条件下，2-氨基苯甲酰胺与芳香醛和脂肪醛的反应。在水介质中，产物形成良好产率。
• Synthesis of quinazolin-4(3H)-ones via electrochemical decarboxylative cyclization of α‑keto acids with 2-aminobenzamides
  作者：Qing Tian、Jinli Zhang、Liang Xu、Yu Wei

  DOI：10.1016/j.mcat.2020.111345

  日期：2021.1

  Abstract Herein, an environmentally benign electrochemical protocol has been disclosed for the synthesis of quinazolin-4(3H)-one derivatives from readily available α‑keto acids and 2-aminobenzamides. This decarboxylative cyclization process proceeds conveniently in the absence of any homogeneous metal catalysts, bases, or external oxidants. This protocol also features CO2 by-products, mild reaction

  摘要 本文公开了一种环境友好的电化学方案，用于从容易获得的 α-酮酸和 2-氨基苯甲酰胺合成 quinazolin-4(3H)-one 衍生物。这种脱羧环化过程在没有任何均相金属催化剂、碱或外部氧化剂的情况下方便地进行。该协议还具有 CO2 副产物、温和的反应条件（室温和空气气氛）和广泛的底物范围，包括一系列 2,3-二取代喹唑啉酮产品。
• Synergistic catalysis on Fe–N_x sites and Fe nanoparticles for efficient synthesis of quinolines and quinazolinones <i>via</i> oxidative coupling of amines and aldehydes
  作者：Zhiming Ma、Tao Song、Youzhu Yuan、Yong Yang

  DOI：10.1039/c9sc04060a

  日期：——

  this paper, we developed a reusable heterogeneous non-precious iron nanocomposite comprising metallic Fe-Fe3C nanoparticles and Fe-N x sites on N-doped porous carbon, which allows for highly efficient synthesis of quinolines and quinazolinones via oxidative coupling of amines and aldehydes using H2O2 as the oxidant in aqueous solution under mild conditions. A set of quinazolines and quinazolinones

  在本文中，我们开发了一种可重复使用的异质非贵铁纳米复合材料，包含金属 Fe-Fe3C 纳米颗粒和 N 掺杂多孔碳上的 Fe-N x 位点，可通过胺和醛的氧化偶联高效合成喹啉和喹唑啉酮在温和条件下以H2O2为氧化剂水溶液。以高产率合成了一系列喹唑啉和喹唑啉酮类化合物，具有广泛的底物范围和良好的官能团耐受性。表征和控制实验表明，金属 Fe 纳米粒子和内置 Fe-N x 位点之间的协同效应是其出色催化性能的主要原因。此外，铁纳米复合材料可以很容易地回收以供连续使用，而催化活性和选择性没有明显损失。这项工作提供了一种方便且可持续的方法来获取药学相关的 N-杂环。
• Palladium-Catalyzed Carbonylative Synthesis of Quinazolinones from 2-Aminobenzamide and Aryl Bromides
  作者：Xiao-Feng Wu、Lin He、Helfried Neumann、Matthias Beller

  DOI：10.1002/chem.201302182

  日期：2013.9.16

  C from CO! A straightforward procedure for the carbonylative synthesis of quinazolinones from readily available 2-aminobenzamide and aryl bromides has been developed. In the presence of a palladium catalyst, various quinazolinones were produced in moderate to excellent yields. Remarkably, no chromatography was needed for purification (see scheme).

  C从CO！已经开发了一种简单的方法，用于从容易获得的2-氨基苯甲酰胺和芳基溴化物羰基合成羰基喹啉酮。在钯催化剂的存在下，以中等至优异的产率制备了各种喹唑啉酮。显着地，不需要层析来纯化（参见方案）。