2-(4-nitrobenzoyl)quinazolin-4(3H)-one

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(4-nitrobenzoyl)quinazolin-4(3H)-one
• 英文别名: 4-(4-oxo-3,4-dihydroquinazoline-2-carbonyl)benzonitrile；2-(4-nitrobenzoyl)-3H-quinazolin-4-one
• 化学式: C₁₅H₉N₃O₄
• 分子量: 295.254
• InChiKey: GIOTYXMTGMTBCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基苯甲酰胺 、 对硝基苯乙酮 在 N-甲基哌啶 、 sulfur 、 二甲基亚砜 作用下， 反应 16.0h， 以44%的产率得到2-(4-nitrobenzoyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  蒽酰胺和苯乙酮的氧化缩合反应，促进硫磺合成2-芳基喹唑啉-4（3H）-酮。

  摘要：

  据报道，由硫代酸酐，脂肪族或芳香族伯胺和苯乙酮经硫促进的三组分反应可导致密集取代的3-取代的2-芳基喹唑啉-4（3 H）-1 。关键步骤涉及乙苯乙酮甲基选择性氧化的级联反应，然后与邻氨基苯甲酰胺缩合。该反应范围适用于色胺酮和各种3-un取代的2-aroylquinazolin-4（3 H）-one的合成。

  DOI：

  10.1002/adsc.201900371

文献信息

• Green Synthesis of 2-Benzoyl-4-quinazolinones
  作者：Zhijie Li、Yamei Pu、Dezhi Qiu、Xiaoping Zhang、Qingle Zeng

  DOI：10.14233/ajchem.2015.18677

  日期：——

  A catalyst-free synthesis of 2-benzoyl-4-quinazolinones is described here. Anthranilamides and a-haloacetophenones were used as the starting reagents. The effects of molar ratio of reactants, catalyst, solvent, base, temperature and time on the reaction were investigated and then the optimal reaction conditions were achieved. All of the substrates examined under the optimized conditions gave high yields. Compared to traditional synthesis method of 2-benzoyl-4-quinazolinones, this method has several advantages, such as no catalyst, cost saving and environmentally benign process.

  本文描述了一种无催化剂的2-苯甲酰基-4-喹唑啉酮的合成方法。采用邻氨基苯甲酰胺和α-卤代乙酰苯作为起始试剂。研究了反应物摩尔比、催化剂、溶剂、碱、温度和时间对反应的影响，并获得了最佳反应条件。在优化的条件下，所有检测的底物均能获得高产率。与传统的2-苯甲酰基-4-喹唑啉酮合成方法相比，该方法具有无催化剂、节约成本和环境友好的优点。
• Sulfur‐Promoted Synthesis of 2‐Aroylquinazolin‐4(3 <i>H</i> )‐ones by Oxidative Condensation of Anthranilamide and Acetophenones
  作者：Thanh Binh Nguyen、Jing‐ya Hou、Pascal Retailleau

  DOI：10.1002/adsc.201900371

  日期：2019.7.11

  three‐component reaction of isatoic anhydride, primary aliphatic or aromatic amines, and acetophenones leading to densely substituted 3‐substituted 2‐aroylquinazolin‐4(3H)‐ones is reported. The key step involves a cascade reaction of selective oxidation of the methyl group of the acetophenones, followed by a condensation with anthranilamides. The scope of the reaction is applicable to the synthesis of tryptanthrin

  据报道，由硫代酸酐，脂肪族或芳香族伯胺和苯乙酮经硫促进的三组分反应可导致密集取代的3-取代的2-芳基喹唑啉-4（3 H）-1 。关键步骤涉及乙苯乙酮甲基选择性氧化的级联反应，然后与邻氨基苯甲酰胺缩合。该反应范围适用于色胺酮和各种3-un取代的2-aroylquinazolin-4（3 H）-one的合成。
• Substituted 1,2,3-triazolo[1,5-a]quinazolines: synthesis and binding to benzodiazepine and adenosine receptors
  作者：L Bertelli

  DOI：10.1016/s0223-5234(00)90154-5

  日期：2000.3

  displacement of halogen, the corresponding 5-amino derivatives and some analogous derivatives bearing cyclohexylamino and p-toluidino substituents were obtained. The binding assays showed a generalized decrease in the affinity towards the benzodiazepine receptors and confirmed a moderate affinity towards the A(1) adenosine receptors in comparison with the previously studied triazoloquinazoline derivatives

  本文报道了对某些苯乙二氮杂和一些3-乙氧基羰基或3-苯基取代的1,2,3-三唑[1,5-a]的A（1）和A（2A）腺苷受体的生物亲和力的合成和评价。喹唑啉。从合适的氯取代的苯叠氮开始，制备了7或8个氯取代的三唑并喹唑啉系列。还报道了三唑并喹唑啉环的硝化反应和相同环的5位羟基的氯化反应。通过卤素的亲核取代，获得了相应的5-氨基衍生物和带有环己基氨基和对甲苯胺基取代基的一些类似衍生物。
• Direct One-Pot Synthesis of Luotonin F and Analogues via Rational Logical Design
  作者：Yan-ping Zhu、Zhuan Fei、Mei-cai Liu、Feng-cheng Jia、An-xin Wu

  DOI：10.1021/ol303331g

  日期：2013.1.18

  An efficient one-pot synthetic protocol has been proposed for the synthesis of luntonin F from easily available starting materials. Through a rational logical design, multifundamental reactions (iodination, Kornblum oxidation, and annulation) were assembled in one-pot. The developed approach can efficiently synthesize luntonin F and a diversity of analogues.
• Electrochemical oxidative synthesis of 2-benzoylquinazolin-4(3<i>H</i>)-one <i>via</i> C(sp³)–H amination under metal-free conditions
  作者：Yongzhi Hu、Xinhua Ma、Huiqing Hou、Weiming Sun、Shuqing Tu、Mei Wu、Rongkun Lin、Xiuzhi Xu、Fang Ke

  DOI：10.1039/d1cy01230d

  日期：——

  induced C(sp3)–H amination of 2-aminobenzamides with ketones using TBAI as a catalyst was developed, and provided 2-benzoylquinazolin-4(3H)-ones under metal-free conditions. The reaction proceeded using the relatively low-toxicity methanol as the solvent, employed molecular oxygen as the ideal green oxidant in a simple undivided cell, and exhibited high atom economy. The mechanism of this C(sp3)–H amination

  开发了使用 TBAI 作为催化剂的 2-氨基苯甲酰胺与酮的电化学诱导 C(sp 3 )-H 胺化，并在无金属条件下提供了 2-苯甲酰基喹唑啉-4(3 H )-酮。该反应以毒性相对较低的甲醇为溶剂，采用分子氧作为理想的绿色氧化剂，在一个简单的未分体电池中进行，表现出较高的原子经济性。这种 C(sp 3 )-H 胺化策略的机制被认为涉及苯乙酮自由基的产生，并且它很容易进一步氧化形成 2-oxo-2-苯基乙醛。