2-benzo[1,3]dioxol-5-yl-quinazolin-4-tosylate | 1448311-31-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzo[1,3]dioxol-5-yl-quinazolin-4-tosylate
• CAS: 1448311-31-6
• 化学式: C₂₂H₁₆N₂O₅S
• 分子量: 420.445
• InChiKey: JQPSXLXHMUPPGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  87.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  环丙乙炔 、 2-benzo[1,3]dioxol-5-yl-quinazolin-4-tosylate 在 三乙烯二胺 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 C₁₄H₁₁NS⁽¹⁺⁾*Br^(1-) 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以79%的产率得到2-(benzo[d][1,3]dioxol-5-yl)-4-(cyclopropylethynyl)quinazoline
  参考文献：
  名称：

  Synthesis of 4-alkynylquinazolines: Pd–Cu-cocatalyzed coupling of quinazoline-4-tosylates with terminal alkynes using N-heterocyclic carbenes as ligands

  摘要：

  描述了一种以Pd-Cu为共催化剂的反应，将喹唑啉-4-磺酸酯与末端炔烃在N-杂环卡宾（NHC）作为配体的条件下结合，生成4-炔基喹唑啉，产率良好至优异。该转化在温和条件下进行，效率高，这对于专注的化合物库构建具有吸引力。

  DOI：

  10.1039/c4ob00700j

文献信息

• Palladium-Catalyzed Cross-Coupling of 4-(Tosyloxy)quinazolines with H-Phosphonates and Phosphine Oxides: An Efficient Access to 2-(Hetero)aryl-4-phosphorylated Quinazolines
  作者：Yiyuan Peng、Xinglin Ye、Jian Huang、Zhihong Deng

  DOI：10.1055/a-1647-5978

  日期：2022.2

  A series of 2-(hetero)aryl-4-phosphorylated quinazolines was successfully synthesized in moderate to excellent yields via a palladium-catalyzed C–O/P–H cross-coupling reaction of 4-(tosyl­oxy)quinazolines with H-phosphonates and phosphine oxides. This efficient and green methodology provides an alternative straightforward protocol for the introduction of phosphorus groups to quinazoline compounds at

  通过钯催化的 4-（甲苯磺酰氧基）喹唑啉与 H-膦酸酯和氧化膦。这种高效且绿色的方法为通过 C-O 活化将磷基团引入 C4 位的喹唑啉化合物提供了另一种直接的方案。
• Palladium-Catalyzed Cross-Coupling Reactions of 4-Tosyl­oxyquinazolines with Indoles: An Efficient Approach to 4-(1H-Indol-1-yl)quinazolines
  作者：Yiyuan Peng、Xinglin Ye、Jian Huang、Zhihong Deng、Jianjun Yuan

  DOI：10.1055/s-0040-1707356

  日期：2021.1

  exploration of our continuous interests on late-stage derivation of quinozaline core is described. A wide array of 4-(1H-indol-1-yl)quinazolines were obtained in good to excellent yields through palladium-catalyzed cross-coupling of 4-tosyloxyquinazolines with indole derivatives under mild reaction conditions.

  摘要 在本文中，描述了我们对喹唑啉核心的后期衍生的持续兴趣的探索。在温和的反应条件下，通过钯催化的4-甲苯磺酰氧基喹唑啉与吲哚衍生物的交叉偶联，以良好至优异的产率获得了多种4-（1 H-吲哚-1-基）喹唑啉。
• Palladium-Catalyzed Cyanation of Quinazoline-4-tosylates for Access to 4-CN-Functionalized Quinazolines
  作者：Yiyuan Peng、Xu Zhao、Yirong Zhou、Qin Yang、Yepeng Xie、Qiuping Ding、Zhihong Deng、Ming Zhang、Jingshi Xu

  DOI：10.1055/s-0033-1339918

  日期：——

  A highly efficient palladium-catalyzed cyanation of quinazoline-4-tosylates is disclosed. The method is successfully developed for the direct access to various 4-CN-functionalized quinazolines, which are potentially useful as biologically and pharmaceutically active compounds. The reactions were performed under mild conditions using inexpensive copper(I) cyanide as cyano source in good to excellent yields and great functional group diversities.