2-(2-(allylthio)benzo[d]oxazol-5-yl)-1-cyclopentyl-1Hbenzo[d]imidazole-5-carboxylic acid methyl ester | 1354785-08-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-(2-(allylthio)benzo[d]oxazol-5-yl)-1-cyclopentyl-1Hbenzo[d]imidazole-5-carboxylic acid methyl ester
• 英文别名: Methyl 1-cyclopentyl-2-(2-prop-2-enylsulfanyl-1,3-benzoxazol-5-yl)benzimidazole-5-carboxylate；methyl 1-cyclopentyl-2-(2-prop-2-enylsulfanyl-1,3-benzoxazol-5-yl)benzimidazole-5-carboxylate
• CAS: 1354785-08-2
• 化学式: C₂₄H₂₃N₃O₃S
• 分子量: 433.531
• InChiKey: MCCQFQOBKRFEIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-羟基-3-硝基苯甲酸 在 palladium on activated charcoal 、 甲酸铵 、 sodium methylate 、 magnesium sulfate 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 12.69h， 生成 2-(2-(allylthio)benzo[d]oxazol-5-yl)-1-cyclopentyl-1Hbenzo[d]imidazole-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Microwave-Assisted Linear Approach Toward Highly Substituted Benzo[d]oxazol-5-yl-1H-benzo[d]imidazole on Ionic Liquid Support

  摘要：

  A novel and efficient diversity-oriented synthetic approach was employed to access the benzo[d]oxazol-5-yl-1H-, benzo[d]imidazole on ionic liquid support, which helps to absorb microwave irradiation. In this paper, we successfully coupled 4- hydroxy-3-nitrobenzoic acid onto ionic liquid-immobilized o-phenylehediaimine which subsequently underwent an acid mediated, ring closure reaction leading to benzimidazole derivatives. After hydrogenation of the nitro group to an amine, the resulting ionic liquid conjugate was reacted with 1,1-thiocarbonyldiimidazols to yield an ionic liquid tagged-benzoxazol, Final skeletal diversity of the present scaffold was further achieved by S-alkylation with alkyl and aryl bromides. The benzo[d]oxazol-5-, yl-1H-benzo[d]imidazole was finally cleaved smoothly from the ionic liquid support with sodium methoxide in methanol under microwave irradiation. This methodology has provided access to a small, diverse library by straightforward and simple operations and could be applied readily in various drug discovery programs.

  DOI：

  10.1021/co200188g

文献信息

• Microwave-Assisted Linear Approach Toward Highly Substituted Benzo[<i>d</i>]oxazol-5-yl-1<i>H</i>-benzo[<i>d</i>]imidazole on Ionic Liquid Support
  作者：Kaushik Chanda、Barnali Maiti、Chih-Chung Tseng、Chung-Ming Sun

  DOI：10.1021/co200188g

  日期：2012.2.13

  A novel and efficient diversity-oriented synthetic approach was employed to access the benzo[d]oxazol-5-yl-1H-, benzo[d]imidazole on ionic liquid support, which helps to absorb microwave irradiation. In this paper, we successfully coupled 4- hydroxy-3-nitrobenzoic acid onto ionic liquid-immobilized o-phenylehediaimine which subsequently underwent an acid mediated, ring closure reaction leading to benzimidazole derivatives. After hydrogenation of the nitro group to an amine, the resulting ionic liquid conjugate was reacted with 1,1-thiocarbonyldiimidazols to yield an ionic liquid tagged-benzoxazol, Final skeletal diversity of the present scaffold was further achieved by S-alkylation with alkyl and aryl bromides. The benzo[d]oxazol-5-, yl-1H-benzo[d]imidazole was finally cleaved smoothly from the ionic liquid support with sodium methoxide in methanol under microwave irradiation. This methodology has provided access to a small, diverse library by straightforward and simple operations and could be applied readily in various drug discovery programs.