(9CI)-4-甲基嘧啶并[1,2-a]苯并咪唑-2-胺 | 111306-36-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 中文名称: (9CI)-4-甲基嘧啶并[1,2-a]苯并咪唑-2-胺
• 英文名称: 2-amino-4-methylpyrimido<1,2-a>benzimidazole
• 英文别名: 4-Methylpyrimido[1,2-a]benzimidazol-2-amine
• CAS: 111306-36-6
• 化学式: C₁₁H₁₀N₄
• mdl: MFCD01575810
• 分子量: 198.227
• InChiKey: NNXDNJOZGQAYLB-UHFFFAOYSA-N

物化性质

• 熔点：
  319-320 °C(Solv: acetonitrile (75-05-8))
• 沸点：
  364.3±42.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (9CI)-4-甲基嘧啶并[1,2-a]苯并咪唑-2-胺 在 盐酸 作用下， 反应 2.5h， 生成 2-amino-4-methylpyrimido<1,2-a>benzimidazole hydrochloride
  参考文献：
  名称：

  Synthesis of functionalized pyrimido[1,2-a]-benzimidazoles from (benzimidazol-2-yl)cyanamide and ?-dicarbonyl compounds using nickel complexes or salts

  摘要：

  It was found that cyclocondensation of (benzimidazol-2-yl)cyanamide with beta-diketones and beta-ketoesters proceeds in the presence of beta-ketoenolates or nickel(2+) acetate with the formation of 2-aminopyrimido[1,2-a]benzimidazole derivatives. Protonation (deuteration) and methylation of substituted 2-aminopyrimido[1,2-a]benzimidazoles takes place at the N-10 atom, while acylation by carboxylic acid anhydrides gives the 2-acylamino derivatives exclusively.

  DOI：

  10.1007/bf00958851
• 作为产物：
  描述：

  1H-苯并咪唑-2-基氰胺 、 乙酰丙酮 在 盐酸 、 bis(acetylacetonate)nickel(II) 作用下， 生成 (9CI)-4-甲基嘧啶并[1,2-a]苯并咪唑-2-胺
  参考文献：
  名称：

  Synthesis of functionalized pyrimido[1,2-a]-benzimidazoles from (benzimidazol-2-yl)cyanamide and ?-dicarbonyl compounds using nickel complexes or salts

  摘要：

  It was found that cyclocondensation of (benzimidazol-2-yl)cyanamide with beta-diketones and beta-ketoesters proceeds in the presence of beta-ketoenolates or nickel(2+) acetate with the formation of 2-aminopyrimido[1,2-a]benzimidazole derivatives. Protonation (deuteration) and methylation of substituted 2-aminopyrimido[1,2-a]benzimidazoles takes place at the N-10 atom, while acylation by carboxylic acid anhydrides gives the 2-acylamino derivatives exclusively.

  DOI：

  10.1007/bf00958851

文献信息

• Synthesis of ureas, amidines, and guanidines of the pyhimido[1,2-a]benzimidazole series
  作者：M. F. Gordeev、Z. K. Dem'yanets、M. N. Bochkareva、V. A. Dorokhov

  DOI：10.1007/bf00959727

  日期：1991.12

  The reaction of derivatives of 2-aminopyrimido[1,2-a]benzimidazole (APB) with isocyanates or dimethylacetamide dimethylacetals yielded ureas and amidines of the title series. The corresponding guanidines were synthesized by reaction of borylated APB with carbodiimides via boron chelates.
• Cyclocondensation of (benzimidazol-2-yl)cyanamide with acetylacetone in the presence of nickel acetylacetonate
  作者：V. A. Dorokhov、M. F. Gordeev

  DOI：10.1007/bf00959402

  日期：1987.2
• DOROXOV V. A.; GORDEEV M. F., IZV. AN CCCP. CEP. XIM.,(1987) N 2, 458-459
  作者：DOROXOV V. A.、 GORDEEV M. F.

  DOI：——

  日期：——
• Synthesis of functionalized pyrimido[1,2-a]-benzimidazoles from (benzimidazol-2-yl)cyanamide and ?-dicarbonyl compounds using nickel complexes or salts
  作者：V. A. Dorokhov、M. F. Gordeev、Z. K. Dem'yanets、M. N. Bochkareva、V. S. Bogdanov

  DOI：10.1007/bf00958851

  日期：1990.11

  It was found that cyclocondensation of (benzimidazol-2-yl)cyanamide with beta-diketones and beta-ketoesters proceeds in the presence of beta-ketoenolates or nickel(2+) acetate with the formation of 2-aminopyrimido[1,2-a]benzimidazole derivatives. Protonation (deuteration) and methylation of substituted 2-aminopyrimido[1,2-a]benzimidazoles takes place at the N-10 atom, while acylation by carboxylic acid anhydrides gives the 2-acylamino derivatives exclusively.