7-nitro-2-phenyl-4H-3,1-benzoxazin-4-one | 38527-51-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 7-nitro-2-phenyl-4H-3,1-benzoxazin-4-one
• 英文别名: 7-nitro-2-phenyl-4H-benzo[d][1,3]oxazin-4-one；7-Nitro-2-phenyl-benzoxazon; 7-Nitro-benzoyl-anthranil；7-nitro-2-phenyl-benzo[d][1,3]oxazin-4-one；7-nitro-2-phenyl-benz[d][1,3]oxazin-4-one；7-Nitro-2-phenyl-benz[d][1,3]oxazin-4-on；7-nitro-2-phenyl-3,1-benzoxazin-4-one
• CAS: 38527-51-4
• 化学式: C₁₄H₈N₂O₄
• 分子量: 268.229
• InChiKey: VZJBDBHHPHPBKL-UHFFFAOYSA-N

物化性质

• 沸点：
  428.4±24.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 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：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-nitro-2-phenyl-4H-3,1-benzoxazin-4-one 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 3-amino-7-nitro-2-phenyl-3H-quinazolin-4-one
  参考文献：
  名称：

  Synthesis and characterization of quinazoline derivatives: search for hybrid molecule as diuretic and antihypertensive agents

  摘要：

  To explore the pharmacological and structure-activity relationship of a series of N-substituted-(4-oxo-2-substituted-phenylquinazolin-3-(4H)-yl), substituted benzene sulfonamide derivatives (1-25) were synthesized from substituted anthranilic acids derived amino quinazolines and substituted benzene sulphonamides. All the synthesized compounds were evaluated for their diuretic (by Lipschitz et al. method), antihypertensive activity by non-invasive blood pressure (NIBP) using the tail-cuff method and anti-diabetic potential in rats. Six compounds showing significantly excellent activity were compared with metolazone, prazosin and diazoxide as standards. Compound N-[7-chloro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl]-4 nitrobenzenesulfonamide (20) exhibited most potent of the series.

  DOI：

  10.3109/14756366.2013.845820
• 作为产物：
  描述：

  2-benzoylamino-4-nitro-benzoic acid 在 乙酸酐 作用下， 反应 2.0h， 生成 7-nitro-2-phenyl-4H-3,1-benzoxazin-4-one
  参考文献：
  名称：

  Synthesis and characterization of quinazoline derivatives: search for hybrid molecule as diuretic and antihypertensive agents

  摘要：

  To explore the pharmacological and structure-activity relationship of a series of N-substituted-(4-oxo-2-substituted-phenylquinazolin-3-(4H)-yl), substituted benzene sulfonamide derivatives (1-25) were synthesized from substituted anthranilic acids derived amino quinazolines and substituted benzene sulphonamides. All the synthesized compounds were evaluated for their diuretic (by Lipschitz et al. method), antihypertensive activity by non-invasive blood pressure (NIBP) using the tail-cuff method and anti-diabetic potential in rats. Six compounds showing significantly excellent activity were compared with metolazone, prazosin and diazoxide as standards. Compound N-[7-chloro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl]-4 nitrobenzenesulfonamide (20) exhibited most potent of the series.

  DOI：

  10.3109/14756366.2013.845820

文献信息

• Palladium‐Catalyzed Decarboxylative Synthesis of 5 <i>H</i> ‐Benzo[4,5][1,3]oxazino[2,3‐ <i>a</i> ]isoindole‐5,11(6a <i>H</i> )‐Diones using 2‐Phenyl‐4 <i>H</i> ‐Benzo[ <i>d</i> ][1,3]oxazin‐4‐Ones and α‐Oxo Carboxylic Acids
  作者：Ram Sunil Kumar Lalji、Prashant Kumar、Mohit Gupta、Virinder S. Parmar、Brajendra K. Singh

  DOI：10.1002/adsc.201901142

  日期：2020.2.6

  A Pd‐catalyzed novel and efficient protocol has been developed for the direct functionalization of 2‐phenyl‐4H‐benzo[d][1,3]oxazin‐4‐ones with α‐oxo carboxylic acids resulting in 5H‐benzo[4,5][1,3]oxazino[2,3‐a]isoindole‐5,11(6aH)‐diones using (NH4)2S2O8 as effective oxidant and AgNO3 as co‐oxidant. All the explored substrates were found to be compatible for this transformation and delivered the corresponding

  已开发出一种Pd催化的新颖有效的方案，可将2-苯基-4- H-苯并[ d ] [1,3]恶嗪-4-酮与α-氧代羧酸直接官能化，生成5 H-苯并[ 4,5] [1,3]恶嗪基[2,3 - a ]异吲哚-5,11 （6a H）-二酮使用（NH 4）2 S 2 O 8作为有效氧化剂，AgNO 3作为共氧化剂。发现所有探索的底物均适用于该转化，并以中等至优异的产率递送了相应的所需产物。
• 4H-Benzo[d][1,3]oxazin-4-ones and Dihydro Analogs from Substituted Anthranilic Acids and Orthoesters
  作者：Joel K. Annor-Gyamfi、Richard A. Bunce

  DOI：10.3390/molecules24193555

  日期：——

  (±)-2-alkyl/aryl-2-ethoxy-1,2-dihydro-4H-benzo[d][1,3]oxazin-4-ones. The formation of the dihydro analogs correlated with the electron density on the aromatic ring: Electron-donating groups favored the 4H- benzo[d][1,3]oxazin-4-ones, while electron-withdrawing groups tended to favor the dihydro product. Substituting a pyridine ring for the benzene ring in the substrate acid suppressed the reaction.

  已开发出一种制备 2-烷基和 2-芳基-4H-苯并[d][1,3]恶嗪-4-酮（也称为 4H-3,1-苯并恶嗪-4-酮）的一锅法，并学习了。该方法包括芳基取代的邻氨基苯甲酸与原酸酯在乙醇中的乙酸催化反应。此外，我们还研究了微波条件下的反应。并非所有底物都能成功产生目标杂环，因为一些反应未能进行最终消除。该过程导致 (±)-2-烷基/芳基-2-乙氧基-1,2-二氢-4H-苯并[d][1,3]恶嗪-4-酮的分离。二氢类似物的形成与芳环上的电子密度相关：给电子基团有利于 4H-苯并[d][1,3]恶嗪-4-酮，而吸电子基团有利于二氢产物.
• Potential Biologically Active Agents, XXVII: Synthesis of Some 4-Substituted Phenylmercaptoacetic Acids
  作者：Rajendra S. Varma、Surendra Bahadur、Anil K. Agnihotri

  DOI：10.1002/ardp.19813140202

  日期：——

  Condensation of 4‐(3H)‐quinazolinone (2) with 4‐(aminophenyl)‐mercaptoacetic acid under the conditions of the Mannich reaction furnished compounds 3a and 3b. Reaction of 4 with 4‐(amino‐phenyl)mercaptoacetic acid yielded 5 which when treated with aryl aldehydes gave 6. Similarly, compounds 8 were obtained from 7.

  4-(3H)-喹唑啉酮 (2) 与 4-(氨基苯基)-巯基乙酸在曼尼希反应条件下缩合得到化合物 3a 和 3b。4 与 4-（氨基-苯基）巯基乙酸反应得到 5，当用芳醛处理时得到 6。同样，化合物 8 由 7 得到。
• Ruggli; Leonhardt, Helvetica Chimica Acta, 1924, vol. 7, p. 906
  作者：Ruggli、Leonhardt

  DOI：——

  日期：——
• Synthesis of Quinoline-Based Thieno-Seleno-Phenylquinazolinones
  作者：H. R. Prakash Naik、H. S. Bhojya Naik、T. R. Ravikumar Naik、M. Raghavendra、T. Aravinda、D. S. Lamani

  DOI：10.1080/10426500802176945

  日期：2009.2.3

  The synthesis of quinoline-substituted phenylquinazolinones containing sulfur and selenium is described. These molecules were isolated from a series of reactions of 2-phenyl-4H-3,1-benzoxazin-4-one with 2-chloro, 2-thieno, and 2-selenoquinoline-3-carbaldehyde hydrazones. The structure of the isolated compounds has been elucidated on the basis of IR, 1H NMR, mass spectral, and elemental analysis data.