N-tert-butyl-2-(naphthalen-2-yl)imidazo[1,2-a]pyrazin-3-amine | 1395407-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-tert-butyl-2-(naphthalen-2-yl)imidazo[1,2-a]pyrazin-3-amine
• 英文别名: Imidazo[1,2-a]pyrazin-3-amine, N-(1,1-dimethylethyl)-2-(2-naphthalenyl)-；N-tert-butyl-2-naphthalen-2-ylimidazo[1,2-a]pyrazin-3-amine
• CAS: 1395407-96-1
• 化学式: C₂₀H₂₀N₄
• 分子量: 316.406
• InChiKey: GJLAUBFLNDBOFZ-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  对溴甲苯 、 N-tert-butyl-2-(naphthalen-2-yl)imidazo[1,2-a]pyrazin-3-amine 在 palladium diacetate 、 potassium carbonate 、 三苯基膦 、 三甲基乙酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以61%的产率得到N-(tert-butyl)-2-(naphthalen-2-yl)-6-(p-tolyl)imidazo[1,2-a]pyrazin-3-amine
  参考文献：
  名称：

  C–H Bond Functionalization Under Metalation–Deprotonation Process: Regioselective Direct Arylation of 3-Aminoimidazo[1,2-a]pyrazine

  摘要：

  Concerted metalation deprotonation (CMD) approach with appropriate proton shuttle precursor, base, and solvent (PivOH-K2CO3-toluene) has rendered a regioselective Pd-catalyzed C6-arylation of 3-aminoimidazo[1,2-a]pyrazine, a therapeutically relevant scaffold accessible by multicomponent reaction. The arylation of this heteroarene suffers from competing C5 and C2'-arylation reactions, while the developed process has virtually eliminated these competing arylations. Density functional calculations for CMD C-H activation at C6, C5, C8, and C2' sites imply that the energy barrier with distortion energy penalty as major contributing component influences the regioselectivity.

  DOI：

  10.1021/jo301065s