4-Methoxybenzo<2,7>naphthyridin-5-one | 160623-58-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-Methoxybenzo<2,7>naphthyridin-5-one
• 英文别名: 4-methoxy-6H-benzo[c][2,7]naphthyridin-5-one
• CAS: 160623-58-5
• 化学式: C₁₃H₁₀N₂O₂
• 分子量: 226.235
• InChiKey: GMGKBQAIBXEBQW-UHFFFAOYSA-N

物化性质

• 沸点：
  333.959±30.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.287±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-Methoxybenzo<2,7>naphthyridin-5-one 在 四(三苯基膦)钯 吡啶 、 三丁基氯化锡 、 三溴化硼 、 苯基锂 、 lithium chloride 作用下， 以 二氯甲烷 为溶剂， 反应 79.33h， 生成 5-(4-Pyridyl)benzo<2,7>naphthyridin-4-one
  参考文献：
  名称：

  Combined Metalation-Palladium-Catalyzed Cross Coupling Strategies. A Formal Synthesis of the Marine Alkaloid Amphimedine

  摘要：

  The synthesis of 5-(4-pyridyl)benzo[c][2,7]naphthyridin-4-one (4), an intermediate previously employed in a total synthesis of the marine alkaloid, amphimedine (2), is reported. The route comprises the Pd-catalyzed Suzuki cross coupling of pyridylborane 21 with 2-iodoaniline to give the azabiaryl 22, which upon LDA-mediated cyclization and triflation leads to benzonaphthyridine 5. Stille cross coupling of 5 with pyridylstannane 24 affords the pyridylbenzonaphthyridine 25, which upon BBr3 treatment leads to the target molecule 4. Pyridine directed ortho metalation chemistry leading to halonicotinate ester 12 and amides 14a,b and cross coupling to benzonaphthyridinones 17, 18 (one-pot procedure) and azabiaryls 20a,b are also reported.

  DOI：

  10.1021/jo00107a004
• 作为产物：
  描述：

  3-Diisopropylaminocarbonyl-2-methoxypyridine 在 四(三苯基膦)钯 sodium hydroxide 、 正丁基锂 、 9-methoxy-BBN 、 二异丙胺 作用下， 以 正己烷 为溶剂， 反应 34.0h， 生成 4-Methoxybenzo<2,7>naphthyridin-5-one
  参考文献：
  名称：

  Combined Metalation-Palladium-Catalyzed Cross Coupling Strategies. A Formal Synthesis of the Marine Alkaloid Amphimedine

  摘要：

  The synthesis of 5-(4-pyridyl)benzo[c][2,7]naphthyridin-4-one (4), an intermediate previously employed in a total synthesis of the marine alkaloid, amphimedine (2), is reported. The route comprises the Pd-catalyzed Suzuki cross coupling of pyridylborane 21 with 2-iodoaniline to give the azabiaryl 22, which upon LDA-mediated cyclization and triflation leads to benzonaphthyridine 5. Stille cross coupling of 5 with pyridylstannane 24 affords the pyridylbenzonaphthyridine 25, which upon BBr3 treatment leads to the target molecule 4. Pyridine directed ortho metalation chemistry leading to halonicotinate ester 12 and amides 14a,b and cross coupling to benzonaphthyridinones 17, 18 (one-pot procedure) and azabiaryls 20a,b are also reported.

  DOI：

  10.1021/jo00107a004

文献信息

• Combined Metalation-Palladium-Catalyzed Cross Coupling Strategies. A Formal Synthesis of the Marine Alkaloid Amphimedine
  作者：F. Guillier、F. Nivoliers、A. Godard、F. Marsais、G. Queguiner、M. A. Siddiqui、V. Snieckus

  DOI：10.1021/jo00107a004

  日期：1995.1

  The synthesis of 5-(4-pyridyl)benzo[c][2,7]naphthyridin-4-one (4), an intermediate previously employed in a total synthesis of the marine alkaloid, amphimedine (2), is reported. The route comprises the Pd-catalyzed Suzuki cross coupling of pyridylborane 21 with 2-iodoaniline to give the azabiaryl 22, which upon LDA-mediated cyclization and triflation leads to benzonaphthyridine 5. Stille cross coupling of 5 with pyridylstannane 24 affords the pyridylbenzonaphthyridine 25, which upon BBr3 treatment leads to the target molecule 4. Pyridine directed ortho metalation chemistry leading to halonicotinate ester 12 and amides 14a,b and cross coupling to benzonaphthyridinones 17, 18 (one-pot procedure) and azabiaryls 20a,b are also reported.