5-(1,3-benzothiazol-2-yl)-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine | 377757-09-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5-(1,3-benzothiazol-2-yl)-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine
• 英文别名: 2-(3-methyl-1,6-diphenylpyrazolo[3,4-b]pyridin-5-yl)-1,3-benzothiazole
• CAS: 377757-09-0
• 化学式: C₂₆H₁₈N₄S
• 分子量: 418.522
• InChiKey: RKPMOGCOYWNMIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氨基-3-甲基-1-苯基吡唑 、 2-苯并噻唑-2-基-1-苯乙酮 、 对二甲氨基苯甲醛 在 溶剂黄146 作用下， 反应 2.0h， 以90%的产率得到5-(1,3-benzothiazol-2-yl)-3-methyl-1,6-diphenyl-1H-pyrazolo[3,4-b]pyridine
  参考文献：
  名称：

  Dearylation with aromatization on cyclocondensation of 4-(dimethyl-amino)benzaldehyde, 2-phenacylaza-heterocycles, and 1,3-[N,C]dinucleophiles

  摘要：

  Three-component cyclocondensation involving p-(dimethylamino)benzaldehyde, 2-phenacylazahetero-cycle, and a 1,3-[N,C]-nucleophile (3,5-dimethoxyaniline, 6-amino-1,3-dimethylpyrimidine-2,4-dione, 1-amino-3-methyl-5-phenylpyrazole) in boiling acetic acid is accompanied by aromatization of the initially formed annelated 4-(p-dimethylaminophenyl)-3-hetaryl-2-phenyl-1,4-dihydropyridines, the direction of which, with splitting off the dimethylaminophenyl substituent or its retention, is determined by the basicity of the hetaryl residue and the structure of the second ring, constructed on the binucleophile. A possible reaction mechanism is discussed.

  DOI：

  10.1007/s10593-009-0230-x

文献信息

• Dearylation with aromatization on cyclocondensation of 4-(dimethyl-amino)benzaldehyde, 2-phenacylaza-heterocycles, and 1,3-[N,C]dinucleophiles
  作者：I. B. Dzvinchuk

  DOI：10.1007/s10593-009-0230-x

  日期：2009.1

  Three-component cyclocondensation involving p-(dimethylamino)benzaldehyde, 2-phenacylazahetero-cycle, and a 1,3-[N,C]-nucleophile (3,5-dimethoxyaniline, 6-amino-1,3-dimethylpyrimidine-2,4-dione, 1-amino-3-methyl-5-phenylpyrazole) in boiling acetic acid is accompanied by aromatization of the initially formed annelated 4-(p-dimethylaminophenyl)-3-hetaryl-2-phenyl-1,4-dihydropyridines, the direction of which, with splitting off the dimethylaminophenyl substituent or its retention, is determined by the basicity of the hetaryl residue and the structure of the second ring, constructed on the binucleophile. A possible reaction mechanism is discussed.