4'-amino-1'H-spiro[cyclopentane-1,2'-(pyrimido[1,2-a]benzimidazole)]-3'-carbonitrile | 1083171-78-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 4'-amino-1'H-spiro[cyclopentane-1,2'-(pyrimido[1,2-a]benzimidazole)]-3'-carbonitrile
• 英文别名: 4'-amino-1'H-spiro[cyclopentane-1,2'-pyrimido[1,2-a]benzimidazole]-3'-carbonitrile；4-aminospiro[1H-pyrimido[1,2-a]benzimidazole-2,1'-cyclopentane]-3-carbonitrile
• CAS: 1083171-78-1
• 化学式: C₁₅H₁₅N₅
• 分子量: 265.318
• InChiKey: NXORBQNOGVKTJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  79.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氨基苯并咪唑 、 环戊亚基丙二腈 以 乙醇 为溶剂， 反应 0.07h， 以82%的产率得到4'-amino-1'H-spiro[cyclopentane-1,2'-(pyrimido[1,2-a]benzimidazole)]-3'-carbonitrile
  参考文献：
  名称：

  Versatility of Alternative Reaction Media: Water-Mediated Domino and Green Chemical Synthesis of Pyrimido[1,2-a]benzimidazole Under Nonconventional Conditions

  摘要：

  A convenient and clean water-mediated synthesis of a series of 4-amino-2-aryl-1,2-dihydro pyrimido[1,2-a]benzimidazoles (4) is reported using alternative nonconventional energy sources. The products are obtained in shorter times with excellent yields (78-89%) from the multicomponent reaction of 2-aminobenzimidazole (1), malononitrile/ethylcyanoacetate (2a/b), and carbonyl compounds (3). The reaction is found to be general with respect to the cyclic and acyclic carbonyl compounds. The procedure does not involve the use of any additional reagent/catalyst, produces no waste, and represents a green synthetic protocol with high atom economy.

  DOI：

  10.1080/00397910802164732

文献信息

• Microporous zeolite catalyst system: an eco-approach for regioselective synthesis of pyrimidobenzimidazoles
  作者：Kapil Arya、Ravi Tomar

  DOI：10.1007/s11164-013-1441-4

  日期：2015.6

  Microporous zeolite, having well-defined pore sizes, was found to be most efficient catalyst for regioselective synthesis of pyrimidobenzimidazoles. Different kinds of zeolites were studied as supported microporous material and showed quite different catalytic activities due to high acidity, excellent textural parametersm and cage-type 3D porous structure under microwaves, and hold great promise due to excellent reusability properties. The structure of the products was confirmed by spectral and X-ray studies. Furthermore, the reaction was performed over a considerably shorter reaction time and generated significantly higher yields under microwaves than by traditional methods. Ordered microporous materials with well-defined pore sizes are proven as active green catalysts for regioselective synthesis of pyrimidobenzimidazoles. Five kinds of zeolites were studied and showed quite different catalytic activities due to their wide acid sites distributions and various pore structures. The structure of the product was confirmed by NOE and X-ray studies.

  研究发现，具有明确孔径的微孔沸石是嘧啶苯并咪唑区域选择性合成的最有效催化剂。对不同种类的沸石作为支撑微孔材料进行了研究，这些沸石在微波下具有高酸度、优异的纹理参数和笼型三维多孔结构，因而表现出截然不同的催化活性。光谱和 X 射线研究证实了产物的结构。此外，与传统方法相比，在微波条件下进行反应的时间大大缩短，产率显著提高。具有明确孔径的有序微孔材料被证明是嘧啶苯并咪唑区域选择性合成的活性绿色催化剂。研究了五种沸石，由于它们的酸位点分布广泛，孔隙结构各不相同，因此表现出了截然不同的催化活性。通过 NOE 和 X 射线研究证实了产物的结构。