3-tert-Butyl-3,4-dihydropyrrolo<1,2-d><1,2,4>triazin-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 3-tert-Butyl-3,4-dihydropyrrolo<1,2-d><1,2,4>triazin-4-one
• 英文别名: 3H,4H-3-Tert-butylpyrro(1,2-D)(1,2,4)triazin-4-one；3-tert-butylpyrrolo[1,2-d][1,2,4]triazin-4-one
• 化学式: C₁₀H₁₃N₃O
• 分子量: 191.233
• InChiKey: BKVYRJITXUGASZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  37.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,2-二(2-甲基-2-丙基)-3-二氮杂环丙二酮 在 三氟化硼乙醚 、 sodium hydride 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.5h， 生成 3-tert-Butyl-3,4-dihydropyrrolo<1,2-d><1,2,4>triazin-4-one
  参考文献：
  名称：

  Ring enlargement of diaziridinone with 2-substituted pyrrole leading to bicyclic triazine and its transformation to novel mesomeric betaine

  摘要：

  A ring enlargement reaction of a diaziridinone was investigated as a possible method for synthesizing heterobicyclic compounds having a bridgehead nitrogen atom. One of the products was transformed to a mesomeric betaine. Thus, the reaction of N,N'-di-tert-butyldiaziridinone (1) and deprotonated pyrrole-2-carboxaldehyde gave 2,3-di-tert-butyl-1-hydroxy-1,2,3,4-tetrahydropyrrolo[1,2-d][1,2,4]-triazin-4-one (4) in good yield. Similarly, 1 was treated with deprotonated imidazole-2-carboxaldehyde to afford the corresponding heterobicycle 5. Under similar conditions, pyrrole-2-carbonitrile gave an acyclic 1:1 adduct, 1-(N,N'-di-tert-butylcarbazoyl)-2-cyanopyrrole (8), which was successfully cyclized under acid catalysis to 2,3-di-tert-butyl-1-imino-1,2,3,4-tetrahydropyrrolo[1,2-d][1,2,4]triazin-4-one (9) and the de-tert-butylated product 10. A novel mesomeric betaine, 2-tert-butylpyrrolo-[1,2-d][1,2,4]triazinium-4-olate (11), was obtained along with its isomer 12 by acidic de-tert-butylation of 4.

  DOI：

  10.1021/jo00076a020