7-bromo-2-phenyl-4H-benzo[d][1,3]oxazin-4-one

• 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-bromo-2-phenyl-4H-benzo[d][1,3]oxazin-4-one
• 英文别名: 7-bromo-2-phenyl-3,1-benzoxazin-4-one
• 化学式: C₁₄H₈BrNO₂
• 分子量: 302.127
• InChiKey: UQEMGNLHSFIFLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 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：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-bromo-2-phenyl-4H-benzo[d][1,3]oxazin-4-one 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成
  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-氨基-4-溴苯甲酸 在 乙酸酐 、 sodium hydroxide 作用下， 反应 3.0h， 生成 7-bromo-2-phenyl-4H-benzo[d][1,3]oxazin-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

• Copper-Catalyzed C-N, C-O Coupling Reaction of Arylglyoxylic Acids with Isatins
  作者：Rashmi Prakash、Sanjib Gogoi

  DOI：10.1002/adsc.201600516

  日期：2016.10.6

  The copper(II)‐catalyzed decarboxylative coupling reactions of arylglyoxylic acids with isatins afford 4H‐benzo[d][1,3]oxazin‐4‐ones via decarbonylation and concurrent C–N, C–O bond formation.

  芳基乙醛酸与Isatin的铜（II）催化的脱羧偶联反应通过脱羰作用和同时的C–N，C–O键形成提供4 H-苯并[ d ] [1,3]恶嗪-4-酮。
• 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。
• Recyclable Heterogeneous Palladium-Catalyzed Carbonylative Cyclization of 2-Iodoanilines with Aryl Iodides Leading to 2-Arylbenzoxazinones
  作者：Zhaotao Xu、Bin Huang、Zebiao Zhou、Mingzhong Cai

  DOI：10.1055/s-0039-1690265

  日期：2020.2

  A highly efficient and practical heterogeneous palladium-catalyzed carbonylative coupling of 2-iodoanilines with aryl iodides has been developed. The reaction occurs smoothly in toluene at 110 °C with N,N-diisopropylethylamine as base under carbon monoxide (5 bar) and offers a general and powerful tool for the construction of various valuable 2-arylbenzoxazinones with excellent atom-economy, high functional

  已经开发了2-碘苯胺与芳基碘化物的高效且实用的钯催化的羰基化偶联。该反应在一氧化碳（5 bar）下以N，N-二异丙基乙胺为碱在110°C的甲苯中顺利进行，它为构建具有优异原子经济性，高官能团的各种有价值的2-芳基苯并恶嗪酮提供了一个通用而有力的工具钯催化剂具有良好的耐受性，良好的高收率和易于回收利用的特点。该反应是从市售易得的2-碘苯胺和碘代芳基制备各种2-芳基苯并恶嗪酮的异相钯催化羰基化偶联的第一个实例。
• Silver and Palladium Cocatalyzed Carbonylative Activation of Benzotriazoles to Benzoxazinones under Neutral Conditions
  作者：Zhiping Yin、Zechao Wang、Xiao-Feng Wu

  DOI：10.1021/acs.orglett.7b03184

  日期：2017.11.17

  A novel and efficient method for the carbonylative activation of benzotriazoles to benzoxazinones has been developed. By using a silver and palladium bimetallic catalyst system, a broad range of benzotriazoles were transformed into the corresponding benzoxazinones in moderate to good yields with excellent functional group tolerance. Notably, this procedure proceeds under neutral conditions.

  已经开发出一种新颖有效的方法，用于苯并三唑羰基化活化为苯并恶嗪酮。通过使用银和钯双金属催化剂体系，各种苯并三唑以中等到良好的收率被转化为相应的苯并三嗪酮，并具有出色的官能团耐受性。值得注意的是，该过程在中性条件下进行。
• Recyclable Heterogeneous Palladium-Catalyzed Cyclocarbonylation of 2-Iodoanilines with Acyl Chlorides in the Biomass-Derived Solvent 2-Methyltetrahydrofuran
  作者：Wenyan Hao、Zhaotao Xu、Zebiao Zhou、Mingzhong Cai

  DOI：10.1021/acs.joc.0c00887

  日期：2020.7.2

  A highly efficient, green palladium-catalyzed cyclocarbonylation of 2-iodoanilines with acyl chlorides has been developed that proceeds smoothly in a biomass-derived solvent 2-methyltetrahydrofuran with N,N-diisopropylethylamine as base at 100 °C under 20 bar of carbon monoxide using an 2-aminoethylamino-modified MCM-41-anchored palladium acetate complex [2N-MCM-41-Pd(OAc)2] as a heterogeneous catalyst

  已开发出一种高效的绿色钯催化的2-碘苯胺与酰氯的绿色钯催化的环羰基化反应，该反应在生物质衍生的溶剂2-甲基四氢呋喃中，以N，N-二异丙基乙胺为碱，在20°C的一氧化碳下于100°C进行。 2-氨基乙基氨基改性的MCM-41锚定的乙酸钯络合物[2N-MCM-41-Pd（OAc）2 ]作为非均相催化剂，产生各种2-取代的4 H-3,1-苯并恶嗪-4-one衍生物，收率良好。该负载的钯催化剂可以通过两步法容易地从容易获得的起始原料中获得，并且可以通过简单的过滤过程容易地回收，并循环至少8次而催化效率没有明显降低。所开发的方法不仅避免使用有毒溶剂，例如四氢呋喃和二甲基甲酰胺，而且解决了昂贵的钯催化剂回收和再利用的基本问题，并有效地防止了所需产物的钯污染。