N-benzoyl-2'-bromo-3-(1-(4-fluorophenyl)vinyl)-1,2,5,6-tetrahydro-2,3'-bipyridine | 1428883-91-3

• 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: N-benzoyl-2'-bromo-3-(1-(4-fluorophenyl)vinyl)-1,2,5,6-tetrahydro-2,3'-bipyridine
• CAS: 1428883-91-3
• 化学式: C₂₅H₂₀BrFN₂O
• 分子量: 463.349
• InChiKey: GQLKIRRLJRUTTR-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-benzoyl-2'-bromo-3-(1-(4-fluorophenyl)vinyl)-1,2,5,6-tetrahydro-2,3'-bipyridine 在 palladium diacetate 、 caesium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以61%的产率得到N-benzoyl-5-(4-fluorophenyl)-1,2,3,4-tetrahydro-1,7-phenanthroline
  参考文献：
  名称：

  Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles

  摘要：

  Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.

  DOI：

  10.1021/jo400246d
• 作为产物：
  描述：

  N-(1-(2-bromopyridin-3-yl)-3-(4-fluorophenyl)prop-2-yn-1-yl)-N-(but-3-en-1-yl)benzamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 乙烯 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以62%的产率得到N-benzoyl-2'-bromo-3-(1-(4-fluorophenyl)vinyl)-1,2,5,6-tetrahydro-2,3'-bipyridine
  参考文献：
  名称：

  Divergent Reaction Pathways of Homologous and Isosteric Propargyl Amides in Sequential Ru/Pd-Catalyzed Annulations for the Synthesis of Heterocycles

  摘要：

  Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.

  DOI：

  10.1021/jo400246d