N-benzoyl-2-(2-bromo-4,5-dimethoxyphenyl)-3-(1-phenylvinyl)-1,2,5,6-tetrahydropyridine | 1428883-86-6

• 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: N-benzoyl-2-(2-bromo-4,5-dimethoxyphenyl)-3-(1-phenylvinyl)-1,2,5,6-tetrahydropyridine
• CAS: 1428883-86-6
• 化学式: C₂₈H₂₆BrNO₃
• 分子量: 504.423
• InChiKey: FKSHCTDLOMOASW-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  N-benzoyl-2-(2-bromo-4,5-dimethoxyphenyl)-3-(1-phenylvinyl)-1,2,5,6-tetrahydropyridine 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78%的产率得到(4aR*,5aR*,9bS*)-N-benzoyl-7,8-dimethoxy-5a-phenyl-2,5,5a,9b-tetrahydro-1H-cyclopropa[2,3]indeno[1,2-b]pyridine
  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-bromo-4,5-dimethoxyphenyl)-3-phenylprop-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87%的产率得到N-benzoyl-2-(2-bromo-4,5-dimethoxyphenyl)-3-(1-phenylvinyl)-1,2,5,6-tetrahydropyridine
  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