2H-1,2,3-三唑-4,5-二甲酰胺 | 388623-87-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2H-1,2,3-三唑-4,5-二甲酰胺
• 英文名称: 2H-[1,2,3]triazole-4,5-dicarboxylic acid diamide
• 英文别名: 2H-1,2,3-Triazole-4,5-dicarboxamide；2H-triazole-4,5-dicarboxamide
• CAS: 388623-87-8；99903-79-4
• 化学式: C₄H₅N₅O₂
• mdl: MFCD00994338
• 分子量: 155.116
• InChiKey: HDIBQANHVXCQBC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-氰基-1H-1,2,3-三唑-5-甲酰胺 在 盐酸 、 溶剂黄146 作用下， 反应 1.0h， 以85%的产率得到2H-1,2,3-三唑-4,5-二甲酰胺
  参考文献：
  名称：

  Novel 2H-1,2,3-Triazole sodium complex from N-[2-amino-1,2-dicyanovinyl]alkanamides

  摘要：

  Diazotization at 0 degrees C of N-[2-amino-1,2-dicyanovinyl]ethanamide 2a or propanamide 2b prepared from diaminomaleonitrile (DAMN) I using aqueous acetic acid and NaNO2 solution furnished sodium complex 3. The X-ray structure of the complex 3 showed that it is a 1:1 mixture of the neutral 2H-triazole heterocycle 4ii and its anion deprotonated at the central (N) atom of the ring, together with a sodium counter ion and two coordinated water molecules. However, when the diazotization reaction was carried out in the presence of aqueous HCl, the product was 5-cyano-2H-[1,2,3]triazole-4-carboxylic acid amide monohydrate 4ii. Diazotization of DAMN 1 using aqueous HCl furnished 1H-1,2,3-triazole-4,5-dicarbonitrile 5, whereas with acetic acid there was no reaction, and hence no route analogous to that leading to complex 3. The structure of both complex 3 and the triazole monohydrate 4ii were solved using X-ray crystallography, and the compounds under study were fully characterized using spectroscopic techniques.

  DOI：

  10.1016/s0385-5414(07)81094-x

文献信息

• Novel 2H-1,2,3-Triazole sodium complex from N-[2-amino-1,2-dicyanovinyl]alkanamides
  作者：A ALAZMI、P GEORGE、O ELDUSOUQUI

  DOI：10.1016/s0385-5414(07)81094-x

  日期：2007.10.1

  Diazotization at 0 degrees C of N-[2-amino-1,2-dicyanovinyl]ethanamide 2a or propanamide 2b prepared from diaminomaleonitrile (DAMN) I using aqueous acetic acid and NaNO2 solution furnished sodium complex 3. The X-ray structure of the complex 3 showed that it is a 1:1 mixture of the neutral 2H-triazole heterocycle 4ii and its anion deprotonated at the central (N) atom of the ring, together with a sodium counter ion and two coordinated water molecules. However, when the diazotization reaction was carried out in the presence of aqueous HCl, the product was 5-cyano-2H-[1,2,3]triazole-4-carboxylic acid amide monohydrate 4ii. Diazotization of DAMN 1 using aqueous HCl furnished 1H-1,2,3-triazole-4,5-dicarbonitrile 5, whereas with acetic acid there was no reaction, and hence no route analogous to that leading to complex 3. The structure of both complex 3 and the triazole monohydrate 4ii were solved using X-ray crystallography, and the compounds under study were fully characterized using spectroscopic techniques.