3-Amino-5-(4-fluorophenyl)-6-oxo-5,7,8,9-tetrahydrothiazolo[2,3-b]quinazoline-2-carbonitrile | 296761-00-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-Amino-5-(4-fluorophenyl)-6-oxo-5,7,8,9-tetrahydrothiazolo[2,3-b]quinazoline-2-carbonitrile
• 英文别名: 3-amino-5-(4-fluorophenyl)-6-oxo-5,7,8,9-tetrahydro-[1,3]thiazolo[2,3-b]quinazoline-2-carbonitrile
• CAS: 296761-00-7
• 化学式: C₁₇H₁₃FN₄OS
• 分子量: 340.381
• InChiKey: JGWWJDVWRVSWPH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Amino-5-(4-fluorophenyl)-6-oxo-5,7,8,9-tetrahydrothiazolo[2,3-b]quinazoline-2-carbonitrile 在 盐酸羟胺 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 以53%的产率得到3-Amino-10-(4-fluorophenyl)-6,8,9,10-tetrahydro-1H,7H-pyrazolo[3',4':4,5][1,3]thiazolo[2,3-b]quinazolin-9-one
  参考文献：
  名称：

  Synthesis and evaluation of some new fluorinated hydroquinazoline derivatives as antifungal agents

  摘要：

  The key intermediate octahydroquinazoline (1) was obtained in one pot synthesis by a modification of the Biginelli reaction. Compound 1 was allowed to react with phenacyl bromide and bromomalononitrile to furnish thiazolo[2,3-b]quinazoline 3 and 12, respectively. Interaction of compound 12 with formamide, formic acid and phenyl isothiocyanate yielded the corresponding pyrimidino[4',5':4,5]thiazolo[2,3-b] quinazolines 13, 14 and 17, respectively. The structure of the synthesized compounds were elucidated by elemental analyses and spectroscopic analyses. Some of the prepared compounds were tested for their antifungal activity in comparison with tioconazole as a reference fungicide. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00029-x
• 作为产物：
  描述：

  1,3-环己二酮 在 盐酸 、 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 3-Amino-5-(4-fluorophenyl)-6-oxo-5,7,8,9-tetrahydrothiazolo[2,3-b]quinazoline-2-carbonitrile
  参考文献：
  名称：

  Synthesis and evaluation of some new fluorinated hydroquinazoline derivatives as antifungal agents

  摘要：

  The key intermediate octahydroquinazoline (1) was obtained in one pot synthesis by a modification of the Biginelli reaction. Compound 1 was allowed to react with phenacyl bromide and bromomalononitrile to furnish thiazolo[2,3-b]quinazoline 3 and 12, respectively. Interaction of compound 12 with formamide, formic acid and phenyl isothiocyanate yielded the corresponding pyrimidino[4',5':4,5]thiazolo[2,3-b] quinazolines 13, 14 and 17, respectively. The structure of the synthesized compounds were elucidated by elemental analyses and spectroscopic analyses. Some of the prepared compounds were tested for their antifungal activity in comparison with tioconazole as a reference fungicide. (C) 2000 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(00)00029-x

文献信息

• Synthesis and evaluation of some new fluorinated hydroquinazoline derivatives as antifungal agents
  作者：M.M Ghorab、S.M Abdel-Gawad、M.S.A El-Gaby

  DOI：10.1016/s0014-827x(00)00029-x

  日期：2000.4

  The key intermediate octahydroquinazoline (1) was obtained in one pot synthesis by a modification of the Biginelli reaction. Compound 1 was allowed to react with phenacyl bromide and bromomalononitrile to furnish thiazolo[2,3-b]quinazoline 3 and 12, respectively. Interaction of compound 12 with formamide, formic acid and phenyl isothiocyanate yielded the corresponding pyrimidino[4',5':4,5]thiazolo[2,3-b] quinazolines 13, 14 and 17, respectively. The structure of the synthesized compounds were elucidated by elemental analyses and spectroscopic analyses. Some of the prepared compounds were tested for their antifungal activity in comparison with tioconazole as a reference fungicide. (C) 2000 Elsevier Science S.A. All rights reserved.