1-amino-2-cyano-3,4-dihydro-1'-ethylspiro{benzimidazo[1,2-a]pyridine-3,3'-indolin}-2'-one | 1182004-94-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 1-amino-2-cyano-3,4-dihydro-1'-ethylspiro{benzimidazo[1,2-a]pyridine-3,3'-indolin}-2'-one
• 英文别名: 1-Amino-2-cyano-3,4-dihydro-1'-ethylspiro{benzimidazo[1,2-a]pyridine-3,3'-indolin}-2'-one；1-amino-1'-ethyl-2'-oxospiro[4H-pyrido[1,2-a]benzimidazole-3,3'-indole]-2-carbonitrile
• CAS: 1182004-94-9
• 化学式: C₂₁H₁₇N₅O
• 分子量: 355.399
• InChiKey: CSEKJUAESCVRRV-UHFFFAOYSA-N

物化性质

• 熔点：
  220-222 °C(Solvent: Ethanol)
• 沸点：
  750.7±70.0 °C(predicted)
• 密度：
  1.42±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  87.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-amino-2-cyano-3,4-dihydro-1'-ethylspiro{benzimidazo[1,2-a]pyridine-3,3'-indolin}-2'-one 、 邻苯二胺 在 吡啶 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以40%的产率得到1-amino-2-(1H-benzimidazol-2-yl)-3,4-dihydro-1'-ethylspiro{benzimidazo[1,2-a]pyridine-3,3'-indolin}-2'-one
  参考文献：
  名称：

  Novel syntheses of some new 3,4-dihydrospiro{benzimidazo[1,2-a]pyridine-3,3′-indolin}-2′-one derivatives

  摘要：

  2-Methylbenzimidazole 1 reacted with 3-dicyanomethylidine-1-ethyl-2-oxoindoline 2 in ethyl acetate to afford 1-amino-2-cyano-3,4-dihydro-1'-ethylspiro{benzimidazo[1,2-a]pyridine-3,3'-indolin}-2'-one 6, which was used as a key intermediate in the synthesis of fused spiropolyheterocyclic derivatives of benzimidazopyridopyrimidine and/or benzimidazonaphthyridine nucleus incorporating an indoline moiety.

  DOI：

  10.1007/s00706-008-0013-6
• 作为产物：
  描述：

  2-甲基苯并咪唑 、 N-ethyl isatilidene 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 4.0h， 以70%的产率得到1-amino-2-cyano-3,4-dihydro-1'-ethylspiro{benzimidazo[1,2-a]pyridine-3,3'-indolin}-2'-one
  参考文献：
  名称：

  Novel syntheses of some new 3,4-dihydrospiro{benzimidazo[1,2-a]pyridine-3,3′-indolin}-2′-one derivatives

  摘要：

  2-Methylbenzimidazole 1 reacted with 3-dicyanomethylidine-1-ethyl-2-oxoindoline 2 in ethyl acetate to afford 1-amino-2-cyano-3,4-dihydro-1'-ethylspiro{benzimidazo[1,2-a]pyridine-3,3'-indolin}-2'-one 6, which was used as a key intermediate in the synthesis of fused spiropolyheterocyclic derivatives of benzimidazopyridopyrimidine and/or benzimidazonaphthyridine nucleus incorporating an indoline moiety.

  DOI：

  10.1007/s00706-008-0013-6

文献信息

• A novel one-pot multi-component synthesis of 3,3’-disubstituted oxindole and spirooxindole scaffolds via Sn-catalyzed C(sp³)–H functionalization of azaarenes by sequential Knoevenagel–Michael-cyclization reaction
  作者：Santosh S. Chavan、Mohsinkhan Y. Pathan、Shridhar H. Thorat、Rajesh Gonnade、Shafeek A. R. Mulla

  DOI：10.1039/c5ra16334j

  日期：——

  Sn-catalyzed C(sp³)–H bond functionalization of 2-methyl azaarenes/2-(azaaryl)methanes has been achieved for the first time in a one-pot reaction with isatin and active methylene compounds.

  Sn催化的2-甲基氮杂芳烃/2-(氮杂芳基)甲烷的C(sp³)–H键官能化首次在一个一锅反应中与靛红和活性的亚甲基化合物实现。

• Novel syntheses of some new 3,4-dihydrospiro{benzimidazo[1,2-a]pyridine-3,3′-indolin}-2′-one derivatives
  作者：Maher F. El-Zohry、Thanaa A. Mohamed、Essam M. Hussein

  DOI：10.1007/s00706-008-0013-6

  日期：2009.3

  2-Methylbenzimidazole 1 reacted with 3-dicyanomethylidine-1-ethyl-2-oxoindoline 2 in ethyl acetate to afford 1-amino-2-cyano-3,4-dihydro-1'-ethylspirobenzimidazo[1,2-a]pyridine-3,3'-indolin}-2'-one 6, which was used as a key intermediate in the synthesis of fused spiropolyheterocyclic derivatives of benzimidazopyridopyrimidine and/or benzimidazonaphthyridine nucleus incorporating an indoline moiety.