3-(4-bromophenyl)quinazoline-2,4(1H,3H)-dione | 2400-96-6

• 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: 3-(4-bromophenyl)quinazoline-2,4(1H,3H)-dione
• 英文别名: 3-(4-bromophenyl)-2,4(1H,3H)-quinazolinedione；3-(4-bromophenyl)-1H-quinazoline-2,4-dione
• CAS: 2400-96-6
• 化学式: C₁₄H₉BrN₂O₂
• 分子量: 317.142
• InChiKey: XPDBBMCHGYLCRP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 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：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-(4-bromophenyl)quinazoline-2,4(1H,3H)-dione 在 tetraphosphorus decasulfide 作用下， 反应 0.33h， 以32%的产率得到3-(4-bromophenyl)quinazoline-2,4(1H,3H)-dithione
  参考文献：
  名称：

  Influence of the replacement of the oxo function with the thioxo group on the antimycobacterial activity of 3-aryl-6,8-dichloro-2H-1,3-benzoxazine-2,4(3H)-diones and 3-arylquinazoline-2,4(1H,3H)-diones

  摘要：

  Series of 3-phenyl-6,8-dichloro-2H-1,3-benzoxazine-2,4(3H)-dithiones, 3-arylquinazoline-2,4(1H,3H)-diones and 3-arylquinazoline-2,4(1H,3H)-dithiones were synthesized, and the antimycobacterial activities of the derivatives evaluated in vitro. The compounds were active against Mycobacterium tuberculosis and conditionally pathogenic mycobacteria (Mycobacterium kansasii and Mycobacterium avium). The replacement of oxygen by sulfur in 3-phenyl-6,8-dichloro-2H-1,3-benzoxazine-2,4(3H)-diones and 3-arylquinazoline-2,4(1H,3H)-diones gave rise to an increase of antimycobacterial activity. The most active compound was 3-(3-chlorophenyl)-6,8-dichloro-2H-1,3-benzoxazine-2,4(3H)-dithione. (C) 2001 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(01)01134-x
• 作为产物：
  描述：

  2-氨基-N-(4-溴苯基)苯甲酰胺 在 苯胺 作用下， 反应 2.33h， 生成 3-(4-bromophenyl)quinazoline-2,4(1H,3H)-dione
  参考文献：
  名称：

  Relationships Between the Chemical Structure of Substances and Their Antimycobacterial Activity Against Atypical Strains. Part 18. 3-Phenyl-2H-1,3-benzoxazine-2,4(3H)-diones and Isosteric 3-Phenylquinazoline-2,4(1H,3H)-diones

  摘要：

  合成了一系列在苯环上取代的3-苯基-2H-1,3-苯并噁嗪-2,4(3H)-二酮2和3-苯基喹唑啉-2,4(1H,3H)-二酮5。目标化合物以及中间体被测试对抗结核分枝杆菌、肯萨斯分枝杆菌和埃维分枝杆菌。氮原子替代氧原子导致抗结核活性下降或丧失。2-[(乙氧羰基)氨基]苯甲酰胺4似乎无活性。水杨酰苯胺1和3-苯基-2H-1,3-苯并噁嗪-2,4(3H)-二酮2对结核分枝杆菌和非结核分枝杆菌表现出显著活性（所有化合物的最小抑制浓度在4-250 μmol/l范围内）。化合物的抗结核活性随着苯基上取代基的电子吸引性和疏水性增加而增加。根据基于向量代数的标准，如余弦系数，分析了化合物的抗结核特性。此外，水杨酰苯胺1对经琼脂扩散法测试的其他微生物也具有活性。

  DOI：

  10.1135/cccc19991902

文献信息

• Synthesis, molecular structure and spectroscopic studies of some new quinazolin-4(3H)-one derivatives; an account on the N- versus S-Alkylation
  作者：Mohamed Hagar、Saied M. Soliman、Farahate Ibid、El Sayed H. El Ashry

  DOI：10.1016/j.molstruc.2015.12.007

  日期：2016.3

  nucleophilicity compared to the O-site. In contrast, the S-site is the more nucleophilic centre than the N-atom of the latter. The structures of the synthesized products have been established on the basis of their melting point (m.p), IR and 1HNMR data. The molecular structures of the products were calculated using the DFT B3LYP/6-311G(d,p) method. The electronic and spectroscopic properties (Uv–Vis and

  摘要 分别制备了 3-芳基-1H,3H-喹唑啉-2,4-二酮和 3-芳基-2-巯基-3H-喹唑啉-4-酮的新系列 N-和 S-烷基化产物。通过 SH 和 NH 底物与碘甲烷、溴乙酸乙酯、烯丙基溴、溴丙炔、2-溴乙醇、1,3-二溴丙烷或苯甲酰溴在 DMF 作为溶剂和无水碳酸钾中的有效亲核取代反应获得良好的产率。quinazolin-2,4-dione 有利于 N-烷基化，而 2-mercapto-3H-quinazolin-4-one 则通过 S-烷基化。DFT 反应性研究表明，前者的 N 位与 O 位相比具有更高的亲核性。相比之下，S 位点是比后者的 N 原子更亲核的中心。合成产物的结构是根据它们的熔点（m. p)、IR 和 1HNMR 数据。使用DFT B3LYP/6-311G(d,p)方法计算产物的分子结构。使用相同水平的理论计算电子和光谱特性（Uv-Vis 和 NMR 光谱）。还预测
• An efficient synthesis of quinazoline-2,4-dione derivatives with the aid of a low-valent titanium reagent
  作者：Da-Qing Shi、Guo-Lan Dou、Zheng-Yi Li、Sai-Nan Ni、Xiao-Yue Li、Xiang-Shan Wang、Hui Wu、Shun-Jun Ji

  DOI：10.1016/j.tet.2007.07.011

  日期：2007.9

  A facile synthetic method using low-valent titanium reagent (TiCl4/Zn system) to promote the novel reductive cyclization of 2-nitrobenzamides and triphosgene is described. Sequentially, a series of quinazoline-2,4-diones were synthesized in good yields.

  描述了一种使用低价钛试剂（TiCl 4 / Zn系统）促进2-硝基苯甲酰胺和三光气新型还原环化的简便合成方法。依次，以高收率合成了一系列的喹唑啉-2,4-二酮。
• Oxidative Rearrangement of Isatins with Arylamines Using H₂ O₂ as Oxidant: A Facile Synthesis of Quinazoline-2,4-diones and Evaluation of Their Antibacterial Activity
  作者：Guanghao Shi、Xinwei He、Yongjia Shang、Cheng Yang、Liwei Xiang

  DOI：10.1002/cjoc.201700280

  日期：2017.12

  A green and highly efficient synthetic method for the synthesis of quinazoline‐2,4‐diones with hydrogen peroxide as the terminal oxidant has been developed. The reaction features the mild reaction conditions, broad substrate scope, metal‐free catalysts, and sole byproduct water. A plausible mechanism for this process was proposed. Moreover, an antibacterial activity study was performed to evaluate

  开发了一种绿色高效的合成方法，以过氧化氢为末端氧化剂合成喹唑啉-2,4-二酮。该反应具有温和的反应条件，广泛的底物范围，无金属催化剂和唯一的副产物水。为此过程提出了一个合理的机制。此外，还进行了一项抗菌活性研究，以使用肉汤微稀释法评估对两种革兰氏阴性细菌菌株（大肠杆菌和肺炎克雷伯菌）和两种革兰氏阳性细菌菌株（表皮葡萄球菌和金黄色葡萄球菌）的抗菌活性。
• Rearrangement of 4-imino-(1H,4H)-3,1-benzoxazine-2-ones to 2,4-quinazolinediones via an isocyanate carboxamide intermediate
  作者：Javad Azizian、Morteza Mehrdad、Khosrow Jadidi、Yaghob Sarrafi

  DOI：10.1016/s0040-4039(00)00803-0

  日期：2000.7

  (2-arylcarbamoyphenyl)carbamic acid methyl ester 5, respectively. These conversions proceed through 4-arylimino-(1H,4H)-3,1-benzoxazin-2-one 2 and its ring-opened isocyanate carboxamide isomer 3 as key intermediates.

  的3-芳基亚氨基-2-吲哚满酮反应1与米在CH氯过苯甲酸2氯2或甲醇中，在0℃下通到相应的3-芳基- 2,4-（1 ħ，3 ħ）-quinazolinediones 4和（2 -芳基氨基甲酰基苯基）氨基甲酸甲酯5。这些转化通过4-芳基-（1 H，4 H）-3,1-苯并恶嗪-2-酮2及其开环的异氰酸酯羧酰胺异构体3作为关键中间体进行。
• An Efficient One-Pot Procedure for Preparation of 2,4(1<i>H</i>,3<i>H</i>)-Quinazolinediones and 2-Thioxoquinazolinone Derivatives Under Microwave Irradiation
  作者：Javad Azizian、Ali A. Mohammadi、Ali R. Karimi

  DOI：10.1081/scc-120015771

  日期：2003.1.3

  Abstract An efficient one-pot synthesis of 2,4(1H,3H)-quinazolinediones and 2-thioxoquinazolinone derivatives are given by the condensation of isatoic anhydride, primary amine and urea or thiourea in the absence of organic or inorganic reagents under microwave irradiation.

  摘要 2,4(1H,3H)-喹唑啉二酮和2-硫代喹唑啉酮衍生物的高效一锅合成是通过在微波辐射下，在没有有机或无机试剂的情况下，由靛红酸酐、伯胺和尿素或硫脲的缩合反应得到的。