4-(4-bromophenyl)-N-(4-methoxyphenyl)-4H-1,2,4-triazol-3-amine | 1381877-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-bromophenyl)-N-(4-methoxyphenyl)-4H-1,2,4-triazol-3-amine
• CAS: 1381877-47-9
• 化学式: C₁₅H₁₃BrN₄O
• 分子量: 345.198
• InChiKey: VXCBDTWEQZZAEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.78
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  51.97
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-(4-bromophenyl)-3-(4-methoxyphenyl)thiourea 、 甲酰肼 在 碘 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 生成 4-(4-bromophenyl)-N-(4-methoxyphenyl)-4H-1,2,4-triazol-3-amine 、 N-(4-bromophenyl)-4-(4-methoxyphenyl)-4H-1,2,4-triazol-3-amine
  参考文献：
  名称：

  Tandem synthesis of [1,2,4]-triazoles mediated by iodine—a regioselective approach

  摘要：

  A tandem regioselective one-pot synthesis of 3-amino-[1,2,4]-triazoles has been achieved from 1,3-disubstituted thioureas using molecular iodine. In this one-pot strategy, the intermediate carbodiimide generated in situ from thiourea upon reaction with HCONHNH2 gives diaryl/alkylhydrazinecarboximidamide or acylureidrazone, which then undergoes an intramolecular cyclodehydration to afford the corresponding 3-amino-[1,2,4]-triazole. The product regioselectivity for unsymmetrical 1,3-disubstituted thioureas correlate well with the pK(a)s of the parent amines attached, in which the amine having higher pK(a) goes to the ring nitrogen while the other nitrogen remains flanked as an exocyclic nitrogen of the triazole core. This method is milder and environmentally sustainable giving good to excellent yields of the desired products. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.042