5,10-bis(4-bromophenyl)-1,3,7,9-tetramethyl-3,7-dihydrodipyrazolo[3,4-b:4′,3′-f ][1,7]naphthyridine | 1610410-80-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5,10-bis(4-bromophenyl)-1,3,7,9-tetramethyl-3,7-dihydrodipyrazolo[3,4-b:4′,3′-f ][1,7]naphthyridine
• 英文别名: 8,16-Bis(4-bromophenyl)-3,5,12,14-tetramethyl-4,5,7,10,12,13-hexazatetracyclo[7.7.0.02,6.011,15]hexadeca-1,3,6,8,10,13,15-heptaene；8,16-bis(4-bromophenyl)-3,5,12,14-tetramethyl-4,5,7,10,12,13-hexazatetracyclo[7.7.0.02,6.011,15]hexadeca-1,3,6,8,10,13,15-heptaene
• CAS: 1610410-80-4
• 化学式: C₂₆H₂₀Br₂N₆
• 分子量: 576.293
• InChiKey: AMCJCXDKYWBZIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氨基-1,3-二甲基吡唑 、 4-溴苯基水合乙二醛 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以69%的产率得到5,10-bis(4-bromophenyl)-1,3,7,9-tetramethyl-3,7-dihydrodipyrazolo[3,4-b:4′,3′-f ][1,7]naphthyridine
  参考文献：
  名称：

  Domino Reaction of Arylglyoxals with Pyrazol-5-amines: Selective Access to Pyrazolo-Fused 1,7-Naphthyridines, 1,3-Diazocanes, and Pyrroles

  摘要：

  New multicomponent domino reactions of arylglyoxals with pyrazol-5-amines have been established, providing selective access to unprecedented pyrazolo-fused 1,7-naphthyridines, 1,3-diazocanes, and pyrroles (up to 52 examples). The unreported dipyrazolo-fused 1,7-naphthyridines were regioselectively synthesized through a special double [3 + 2 + 1] heteroannulation accompanied by direct C C formation between two electrophilic sites of arylglyoxals. The unusual [3 + 3 + 1 + 1] cyclization resulted in 20 examples of novel dipyrazolo-fused 1,3-diazocanes, whereas pyrrolo[2,3-c]pyrazoles were obtained in good yields by varying arylglyoxals 1 and pyrazol-5-amines 2 in the ratio 1:2. Mechanisms of formation of these three new types of heterocycles are also proposed.

  DOI：

  10.1021/jo500823z

文献信息

• Domino Reaction of Arylglyoxals with Pyrazol-5-amines: Selective Access to Pyrazolo-Fused 1,7-Naphthyridines, 1,3-Diazocanes, and Pyrroles
  作者：Bo Jiang、Wei Fan、Mu-Yan Sun、Qin Ye、Shu-Liang Wang、Shu-Jiang Tu、Guigen Li

  DOI：10.1021/jo500823z

  日期：2014.6.6

  New multicomponent domino reactions of arylglyoxals with pyrazol-5-amines have been established, providing selective access to unprecedented pyrazolo-fused 1,7-naphthyridines, 1,3-diazocanes, and pyrroles (up to 52 examples). The unreported dipyrazolo-fused 1,7-naphthyridines were regioselectively synthesized through a special double [3 + 2 + 1] heteroannulation accompanied by direct C C formation between two electrophilic sites of arylglyoxals. The unusual [3 + 3 + 1 + 1] cyclization resulted in 20 examples of novel dipyrazolo-fused 1,3-diazocanes, whereas pyrrolo[2,3-c]pyrazoles were obtained in good yields by varying arylglyoxals 1 and pyrazol-5-amines 2 in the ratio 1:2. Mechanisms of formation of these three new types of heterocycles are also proposed.