Benzo<2,7>naphthyridinone 7-oxide | 160623-50-7

• 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: Benzo<2,7>naphthyridinone 7-oxide
• CAS: 160623-50-7
• 化学式: C₁₂H₈N₂O₂
• 分子量: 212.208
• InChiKey: LNMZPZLEXCLKOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.31
• 重原子数：
  16.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  59.8
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  Benzo<2,7>naphthyridinone 7-oxide 在 铁粉 、 三苯基膦 作用下， 以 溶剂黄146 为溶剂， 反应 0.5h， 以99%的产率得到benzo[c][2,7]naphthyridin-5(6H)-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：

  4-Bromo-3-carboxypyridine 1-oxide 在 四(三苯基膦)钯 4-二甲氨基吡啶 、 硼酸三甲酯 、 叔丁基锂 、 sodium carbonate 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.25h， 生成 Benzo<2,7>naphthyridinone 7-oxide
  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.