2-(benzo[b]thiophen-3-yl)quinazolin-4(3H)-one | 1570097-66-3

• 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: 2-(benzo[b]thiophen-3-yl)quinazolin-4(3H)-one
• CAS: 1570097-66-3
• 化学式: C₁₆H₁₀N₂OS
• 分子量: 278.334
• InChiKey: OZDAIJZEJAPEPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.75
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(benzo[b]thiophen-3-yl)quinazolin-4(3H)-one 、 1-[(三异丙基硅烷基)乙炔基]-1,2-苯碘酰-3(1H)-酮 在 silver hexafluoroantimonate 、 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以78%的产率得到2-(2-((triisopropylsilyl)ethynyl)benzo[b]thiophene-3-yl)-quinazolin-4(3H)-one
  参考文献：
  名称：

  Iridium(III)-Catalyzed Alkynylation of 2-(Hetero)arylquinazolin-4-one Scaffolds via C–H Bond Activation

  摘要：

  The directed C-H alkynylation of 2-(hetero)arylquinazolin-4-ones has been explored with the ethynylbenziodoxolone reagent TIPS-EBX employing an Ir(III) catalyst. Complementary conditions for either monoalkynylation or dialkynylation have been developed. Also demonstrated is the broad scope of this reaction and the compatibility of various functional groups such as -F, -Cl, -Br, -CF3, -OMe, -NO2, and alkyl, etc.

  DOI：

  10.1021/acs.joc.8b02738
• 作为产物：
  描述：

  3-甲醛苯并噻吩 、 2-氨基苯甲酰胺 在 对甲苯磺酸 、 碘苯二乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以71%的产率得到2-(benzo[b]thiophen-3-yl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Iridium(III)-Catalyzed Alkynylation of 2-(Hetero)arylquinazolin-4-one Scaffolds via C–H Bond Activation

  摘要：

  The directed C-H alkynylation of 2-(hetero)arylquinazolin-4-ones has been explored with the ethynylbenziodoxolone reagent TIPS-EBX employing an Ir(III) catalyst. Complementary conditions for either monoalkynylation or dialkynylation have been developed. Also demonstrated is the broad scope of this reaction and the compatibility of various functional groups such as -F, -Cl, -Br, -CF3, -OMe, -NO2, and alkyl, etc.

  DOI：

  10.1021/acs.joc.8b02738

文献信息

• Cascade synthesis of quinazolinones from 2-aminobenzonitriles and aryl bromides via palladium-catalyzed carbonylation reaction
  作者：Haoquan Li、Lin He、Helfried Neumann、Matthias Beller、Xiao-Feng Wu

  DOI：10.1039/c3gc42089b

  日期：——

  A cascade synthesis of quinazolinones from 2-aminobenzonitriles and aryl bromides through a palladium-catalyzed carbonylation reaction has been developed. Various quinazolinones were produced in moderate to excellent yields. The reactions go through aminocarbonylation of aryl bromides–hydration of nitriles–cyclization sequence. Notably, all the products were isolated by recrystallization.

  已经开发了通过钯催化的羰基化反应从2-氨基苄腈和芳基溴化物级联合成喹唑啉酮的方法。各种喹唑啉酮以中等至优异的产率生产。该反应通过芳基溴的氨基羰基化反应-腈的水合反应-环化顺序进行。值得注意的是，所有产物通过重结晶分离。