2,3-diphenylimidazo[1,2-c]quinazoline | 52747-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,3-diphenylimidazo[1,2-c]quinazoline
• CAS: 52747-80-5
• 化学式: C₂₂H₁₅N₃
• 分子量: 321.381
• InChiKey: RTBVGJUTQBLSPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-diphenylimidazo[1,2-c]quinazoline 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 以91.1%的产率得到2,3-Diphenyl-5,6-dihydroimidazo[1,2-c]quinazoline
  参考文献：
  名称：

  Imidazo[1,2-c]quinazolines with lipid peroxidation inhibitory effect

  摘要：

  A series of imidazo[1,2-c]quinazolines of different lipophilic character was prepared. According to their antioxidant (cyclic voltammetry) properties they all should be potent inhibitors of lipid peroxidation. Under the given circumstances (NADPH-induced lipid peroxidation in rat brain microsomes and Fe(2+)-induced lipid peroxidation in rat brain homogenate), however, their lipid peroxidation inhibitory activity was strongly dependent on their lipophilicity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80007-x
• 作为产物：
  描述：

  2-(2-硝基苯基)-4,5-二苯基-1H-咪唑 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 2,3-diphenylimidazo[1,2-c]quinazoline
  参考文献：
  名称：

  Imidazo[1,2-c]quinazolines with lipid peroxidation inhibitory effect

  摘要：

  A series of imidazo[1,2-c]quinazolines of different lipophilic character was prepared. According to their antioxidant (cyclic voltammetry) properties they all should be potent inhibitors of lipid peroxidation. Under the given circumstances (NADPH-induced lipid peroxidation in rat brain microsomes and Fe(2+)-induced lipid peroxidation in rat brain homogenate), however, their lipid peroxidation inhibitory activity was strongly dependent on their lipophilicity. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(98)80007-x

文献信息

• An efficient synthesis of quinazoline derivatives with the aid of low-valent titanium reagent
  作者：Daqing Shi、Chunling Shi、Juxian Wang、Liangce Rong、Qiya Zhuang、Xiangshan Wang

  DOI：10.1002/jhet.5570420201

  日期：2005.3

  Quinazolin-4(3H)-ones, 1,2-dihydroquinazolin-4(3H)-ones, 3,4-dihydroquinazolines, imidazo[1,2-c]-quinazolines and 5,6-dihydroimidazo[1,2-c]quinazolines were synthesized by the novel reductive reaction of nitro group, N-H bond and ortho-ester, aldehydes or ketones promoted by the low-valent titanium reagent (TiCl4-Zn system). The structures of these compounds were characterized by elemental analysis

  喹唑啉-4（3 H）-one，1,2-二氢喹唑啉-4（3 H）-one，3,4-二氢喹唑啉，咪唑并[1,2- c ]-喹唑啉和5,6-二氢咪唑并[1,2 - c ^ ]喹唑啉通过将低价钛试剂（促进的TiCl硝基，NH键和原酸酯，醛或酮的新型还原反应，合成4 -Zn系统）。这些化合物的结构通过元素分析，IR和1 HNMR光谱进行表征，并通过单晶X射线衍射分析进一步证实。
• Synthesis of Quinazolinones, Imidazo[1,2-<i>c</i> ]quinazolines and Imidazo[4,5-<i>c</i> ]quinolines through Tandem Reductive Amination of Aryl Halides and Oxidative Amination of C(sp³ )-H Bonds
  作者：Nitesh Kumar Nandwana、Shiv Dhiman、Hitesh Kumar Saini、Indresh Kumar、Anil Kumar

  DOI：10.1002/ejoc.201601329

  日期：2017.1.18

  2-c]quinazolines and imidazo[4,5-c]quinolines. The reaction involves a copper-catalyzed reductive amination through azidation followed by reduction and oxidative amination of C(sp3)–H bonds of N,N-dimethylacetamide in the presence of TBHP (tert-butylhydroperoxide) as oxidant. The method uses the easily available sodium azide as a nitrogen source and DMA (N,N-dimethylacetamide) as a one-carbon source for the

  已经描述了用于合成喹唑啉酮、咪唑并[1,2-c]喹唑啉和咪唑并[4,5-c]喹啉的串联多组分方法。该反应涉及铜催化的叠氮化还原胺化，然后在 TBHP（叔丁基氢过氧化物）作为氧化剂的存在下还原和氧化胺化 N,N-二甲基乙酰胺的 C(sp3)-H 键。该方法使用容易获得的叠氮化钠作为氮源，使用 DMA（N,N-二甲基乙酰胺）作为单碳源合成这些 N-稠合杂环，收率良好。该反应也可用于克级合成。
• Synthesis of Quinazolines and Imidazo[1,2-<i>c</i>]quinazolines with the Aid of a Low-Valent Titanium Reagent
  作者：Daqing Shi、Juxian Wang、Chunling Shi、Liangce Rong、Qiya Zhuang、Hongwen Hu

  DOI：10.1055/s-2004-822893

  日期：——

  A short and facile synthesis of a series of quinazolines and imidazo[1,2-c]quinazolines was accomplished in good yields via the novel reductive cyclization of 2-nitrobenzyl amines or 2-(2-nitrophenyl)imidazoles with ortho-ester, aldehydes or ketones ­promoted by TiCl4/Zn system. The structures were established by spectroscopic data and confirmed by X-ray analysis.

  通过TiCl4/Zn体系促进的2-硝基苄胺或2-(2-硝基苯基)咪唑与邻酯、醛或酮的创新还原环化反应，实现了一系列喹唑啉和咪唑[1,2-c]喹唑啉的简便合成，产率良好。通过光谱数据确定了结构，并通过X射线分析进行了确认。
• Copper-catalyzed tandem Ullmann type C–N coupling and dehydrative cyclization: synthesis of imidazo[1,2-c]quinazolines
  作者：Nitesh K. Nandwana、Shiv Dhiman、Ganesh M. Shelke、Anil Kumar

  DOI：10.1039/c5ob02469b

  日期：——

  A simple and efficient one-pot protocol has been demonstrated for the synthesis of imidazo[1,2-c]quinazoline derivatives through a copper catalyzed tandem reaction between substituted 2-(2-bromophenyl)-1H-imidazoles and formamide. The synthetic protocol involves initial Ullmann-type C–N coupling followed by intramolecular dehydrative cyclization. The method uses readily available 2-(2-bromophenyl)-1H-imidazoles

  已经证明了一种简单有效的一锅操作规程，用于通过取代的2-（2-溴苯基）-1 H-咪唑与甲酰胺之间的铜催化串联反应合成咪唑并[1,2- c ]喹唑啉衍生物。合成方案包括最初的Ullmann型C–N偶联，然后进行分子内脱水环化。该方法使用容易获得的2-（2-溴苯基）-1- ħ -咪唑作为起始物质，得到咪唑并[1,2 Ç ]喹唑啉在中度至良好的产率和提供610毫克（71％）的产率3a中从一个克规模反应。
• Design of Photosensitive Cobalt Complex Intermediates and Their Application in the Green Syntheses of Molecules Containing the Quinazolin-4(3<i>H</i>)-imine Scaffold
  作者：Xianwei Zhang、Tianzhao Wang、Shisheng Cui、Lei Li、Zhibing Zheng、Chunlai Mi、Bin Lin、Xuhong Ren、Xinhua He

  DOI：10.1021/acs.joc.1c02987

  日期：2022.7.1

  of Co(II) and two substrate molecules, bind to O2 and absorb visible light over a wide spectral range, triggering in situ oxidative decarboxylation to produce molecules containing the quinazolin-4(3H)-imine scaffold. These reactions employed glyoxylic acid and ketoacids as new building blocks, and good to excellent yields of the corresponding products were obtained under mild reaction conditions using

  钴/光氧化还原协同催化是一种成熟的可见光光氧化还原催化技术。最近，Co(II)配合物在均相催化中的光敏性引起了科学家们的兴趣。在这项研究中，光敏 Co(II) 复合中间体旨在开发新的合成方法。这些中间体由 Co(II) 和两个底物分子组成，与 O 2结合并吸收宽光谱范围内的可见光，触发原位氧化脱羧生成含有 quinazolin-4(3 H)-亚胺支架。这些反应采用乙醛酸和酮酸作为新的结构单元，在温和的反应条件下，使用绿色且廉价的试剂和溶剂，获得了良好至优异的相应产物产率。这些结果很重要，因为钴基光敏中间体的设计将有助于建立利用可见光的新方法，从而导致有机合成的创新。