2-(N,N-dimethylamino)-5-nitrobenzoxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-(N,N-dimethylamino)-5-nitrobenzoxazole
• 英文别名: N,N-dimethyl-5-nitro-1,3-benzoxazol-2-amine
• 化学式: C₉H₉N₃O₃
• 分子量: 207.189
• InChiKey: HUOWNZKWLMNANK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氯苯并恶唑 在 硫酸 、 硝酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 2-(N,N-dimethylamino)-5-nitrobenzoxazole
  参考文献：
  名称：

  SYNTHESIS OF NEW TETRACYCLE FUSED ACRIDINE ANALOGUES BEARING OXAZOLE RING

  摘要：

  New acridine derivatives have been prepared via Ullman condensation involving benzoxazole (5) and 2-bromo-benzoic acid. Linear products were obtained. The structure of oxazolo[4,5-b]acridine was determined by NMR spectroscopy.

  DOI：

  10.1081/scc-120003145

文献信息

• Utilization of carbon disulfide as a powerful building block for the synthesis of 2-aminobenzoxazoles
  作者：Tirumaleswararao Guntreddi、Bharat Kumar Allam、Krishna Nand Singh

  DOI：10.1039/c3ra41189c

  日期：——

  This protocol describes a novel, mild and convenient route to afford 2-aminobenzoxazoles in high yields, and represents a significant advance towards an environmentally friendly strategy. Aliphatic amines are made to react with carbon disulfide to provide intermediate dithiocarbamates (DTC), which in the presence of 2-aminophenol, subsequently undergo successive intermolecular nucleophilic attack and desulfurization to produce 2-aminobenzoxazoles within 3 h.

  此协议描述了一条新颖、温和且便捷的途径，能够在高产率下制备2-氨基苯并噁唑，标志着向环境友好型策略迈出了重要的一步。脂肪族胺与二硫化碳反应生成中间体二硫代氨基甲酸盐（DTC），在2-氨基苯酚的存在下，这些中间体随后经历连续的分子间亲核攻击和脱硫反应，在3小时内即可生成2-氨基苯并噁唑。
• Selective synthesis of 2-aminobenzoxazoles and 2-mercaptobenzoxazoles by using o-aminophenols as starting material
  作者：Min Liu、Meng-Tian Zeng、Wan Xu、Li Wu、Zhi-Bing Dong

  DOI：10.1016/j.tetlet.2017.09.092

  日期：2017.11

  dithiocarbamates and tetramethylthiuram disulfide (TMTD), respectively. With the promotion of NaH/CuI, the reaction of o-aminophenols with dithiocarbamates gave 2-aminobenzoxazoles with good yield (70–92%) in one pot manner, and 2-mercaptobenzoxazoles were synthesized (yield: 55–80%) in the presence of K2CO3 by treating o-aminophenols with tetramethylthiuram disulfide (TMTD). The feature of this method

  通过分别用二硫代氨基甲酸酯和四甲基秋兰姆二硫化物（TMTD）处理邻氨基苯酚来选择性合成2-氨基苯并恶唑和2-巯基苯并恶唑。随着NaH / CuI的促进，邻氨基苯酚与二硫代氨基甲酸酯的反应可以一锅法得到2-氨基苯并恶唑，收率良好（70-92％），而合成2-巯基苯并恶唑（收率：55-80％）。通过用二甲基四甲基秋兰姆（TMTD）处理邻氨基苯酚来获得K 2 CO 3的存在。该方法的特征包括良好到极好的收率，容易的操作和广泛的底物范围，这使得该方案在制备某些潜在的药物活性化合物中具有实用性和吸引力。
• Silver-Mediated Direct Amination of Benzoxazoles: Tuning the Amino Group Source from Formamides to Parent Amines
  作者：Seung���Hwan Cho、Ji���Young Kim、S.���Yunmi Lee、Sukbok Chang

  DOI：10.1002/anie.200903957

  日期：2009.11.16

  Going to the source: Formamides or parent amines were used as an amino group source for the silver‐mediated amination of benzoxazoles. Although reactions with formamides proceeded at high temperatures, the direct amination with amines took place under much milder conditions (see scheme). Optically active amino groups could also be installed without racemization.

  来源：甲酰胺或母体胺被用作氨基介导的苯并恶唑的银基胺化反应。尽管与甲酰胺的反应在高温下进行，但与胺的直接胺化反应却在温和得多的条件下进行（参见方案）。光学活性的氨基也可以不消旋地安装。
• Copper catalyzed synthesis of benzoxazoles and benzothiazoles via tandem manner
  作者：Wan Xu、Meng-Tian Zeng、Sha-Sha Liu、Yue-Sheng Li、Zhi-Bing Dong

  DOI：10.1016/j.tetlet.2017.09.089

  日期：2017.11

  catalysis of copper, 2-aminophenols or 2-aminothiophenols reacted with thiocarbamoyl chlorides via a tandem manner, furnishing a series of 17 benzoheterocycles smoothly with good to excellent yields (70–91%). The broad substrate scope, short reaction time, mild react conditions, easy performance and nice yields make this approach attractive, showing its practical synthetic value for the preparation of some

  提出了用于制备取代的2-氨基苯并恶唑和2-氨基苯并噻唑的有用方案。在铜的催化下，2-氨基苯酚或2-氨基硫代苯酚与硫代氨基甲酰氯通过串联方式反应，可顺利提供一系列17个苯并杂环，并具有良好或优异的收率（70-91％）。广泛的底物范围，短的反应时间，温和的反应条件，容易的操作和良好的收率使该方法具有吸引力，显示出其对某些生物或药物活性化合物的制备的实用合成价值。
• Transition metal-free direct amination of benzoxazoles using formamides as nitrogen sources
  作者：Rui Wang、Hong Liu、Liang Yue、Xiao-ke Zhang、Qiu-yuan Tan、Ruo-lin Pan

  DOI：10.1016/j.tetlet.2014.02.070

  日期：2014.4

  A transition metal-free method for the direct amination of benzoxazoles using formamides as nitrogen sources is reported, which was mediated by an inexpensive and environmentally friendly tetrabutylammonium iodide/tert-butyl hydroperoxide system and gave the 2-aminobenzoxazole derivatives with moderate to good yields.

  报道了一种使用甲酰胺作为氮源的无过渡金属直接胺化苯并恶唑的方法，该方法由廉价且环保的碘化四丁基铵/叔丁基氢过氧化物体系介导，并以中等至良好的收率得到了2-氨基苯并恶唑衍生物。