5-morpholino-2-phenyl-4-(4-amino-1,2,4-triazol-3-yl)-1,2,3-triazol | 134426-04-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-morpholino-2-phenyl-4-(4-amino-1,2,4-triazol-3-yl)-1,2,3-triazol
• 英文别名: 3-(5-Morpholin-4-yl-2-phenyltriazol-4-yl)-1,2,4-triazol-4-amine
• CAS: 134426-04-3
• 化学式: C₁₄H₁₆N₈O
• 分子量: 312.334
• InChiKey: GWYKJRRGUNFATF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  99.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (苯基亚肼基)丙二腈 在 吡啶 、 copper (I) acetate 、 一水合肼 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.5h， 生成 5-morpholino-2-phenyl-4-(4-amino-1,2,4-triazol-3-yl)-1,2,3-triazol
  参考文献：
  名称：

  Synthese und Reaktionen von 2-Arylhydrazono-2-cyan-N,N-dialkyl-acetamidinen

  摘要：

  The title compounds 3 were synthesized by reaction of arlyhydrazono-malononitriles 1 with secondary amines and used for subsequent cyclization reactions. Thus, 3 undergoes cyclooxidation by treatment with CuSO4/pyridine to form the 5-dialkylamino-2-aryl-1,2,3-triazolo-4-carbonitriles 4. From 4 a and hydrazine hydrate/DMF the 4-(1,3,4-triazolyl-5)-1,2,3-triazole 5 c is obtainable. The chloroacetylation of 3 is accompanied by hydrolysis of the amino group to yield the arylhydrazono-N-chloracetyl cyanoacetamides 6. The quaternisation of 6 with pyridins is followed by the Thorpe cyclization to form the 4-amino-5-arylazo-6-hydroxy-3-pyridinio-pyrid-2-on-chlorides 8, useful as cationic dyes. The reaction of 3 with trichloroacetonitriles yields the 5-arylazo-4-imino-2-trichlormethyl-1,4-dihydropyrimidines 10 a-c which can be converted into the 5-arylazo-2-hydrazino-pyrimidine derivatives 10 d-f.From 10 d the 6-phenylazo-triazolo[4,3-a]pyrimidine derivative 11 is obtainable. From 3 and phenylisothiocyanate the 5-arylazo-4-imino-1,4-dihydropyrimidin-2-thiones 12 arise. The structures were investigated by C-13-NMR-spectroscopy.

  DOI：

  10.1007/bf00809365

文献信息

• SCHAFER, H.;GEWALD, K.;BELLMANN, P.;GRUNER, M., MONATSH. CHEM., 122,(1991) N, C. 195-207
  作者：SCHAFER, H.、GEWALD, K.、BELLMANN, P.、GRUNER, M.

  DOI：——

  日期：——
• Synthese und Reaktionen von 2-Arylhydrazono-2-cyan-N,N-dialkyl-acetamidinen
  作者：H. Sch�fer、K. Gewald、P. Bellmann、M. Gruner

  DOI：10.1007/bf00809365

  日期：1991.3

  The title compounds 3 were synthesized by reaction of arlyhydrazono-malononitriles 1 with secondary amines and used for subsequent cyclization reactions. Thus, 3 undergoes cyclooxidation by treatment with CuSO4/pyridine to form the 5-dialkylamino-2-aryl-1,2,3-triazolo-4-carbonitriles 4. From 4 a and hydrazine hydrate/DMF the 4-(1,3,4-triazolyl-5)-1,2,3-triazole 5 c is obtainable. The chloroacetylation of 3 is accompanied by hydrolysis of the amino group to yield the arylhydrazono-N-chloracetyl cyanoacetamides 6. The quaternisation of 6 with pyridins is followed by the Thorpe cyclization to form the 4-amino-5-arylazo-6-hydroxy-3-pyridinio-pyrid-2-on-chlorides 8, useful as cationic dyes. The reaction of 3 with trichloroacetonitriles yields the 5-arylazo-4-imino-2-trichlormethyl-1,4-dihydropyrimidines 10 a-c which can be converted into the 5-arylazo-2-hydrazino-pyrimidine derivatives 10 d-f.From 10 d the 6-phenylazo-triazolo[4,3-a]pyrimidine derivative 11 is obtainable. From 3 and phenylisothiocyanate the 5-arylazo-4-imino-1,4-dihydropyrimidin-2-thiones 12 arise. The structures were investigated by C-13-NMR-spectroscopy.