2-cyanomethyl-4,5-dihydro-4-oxo-5-(1,3-diphenylpyrazol-4-yl)methylidene thiazoline | 864669-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-cyanomethyl-4,5-dihydro-4-oxo-5-(1,3-diphenylpyrazol-4-yl)methylidene thiazoline
• 英文别名: 2-[5-[(1,3-diphenylpyrazol-4-yl)methylidene]-4-oxo-1,3-thiazol-2-yl]acetonitrile
• CAS: 864669-66-9
• 化学式: C₂₁H₁₄N₄OS
• 分子量: 370.434
• InChiKey: XVGWMMLVBVFXSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.47
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  71.04
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2-cyanomethyl-4,5-dihydro-4-oxo-5-(1,3-diphenylpyrazol-4-yl)methylidene thiazoline 在 哌啶 、 乙酸酐 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 5-ethoxymethyleneamino-2-(1,3-diphenylpyrazol-4-yl)methylidene-3-oxo-6,8-dicyano-2,3,7-trihydro-7-tolyl-thiazolo[3,2-a]pyridine
  参考文献：
  名称：

  A Facile Synthesis of Some New Thiazolo[3, 2]pyridines Containing Pyrazolyl Moiety and Their Antimicrobial Activity

  摘要：

  Condensation of 2-cyanomethyl-4-thiazolinone 1 with 1,3-diphenyl-pyrozole-4-carboxaldehyde 2 in ethanol containing a few drops of piperidine yielded the novel methylene derivative 3. Compound 3 was refluxed with malononitrile to give the corresponding thiazolo[3,2-a]pyridine derivative 5. Also, treatment of compound 3 with benzylidenemalononitriles gave the thiazolo[3,2-a]pyridine derivatives 6a-e. Refluxing of compound 6d with triethyl orthoformate furnished the ethoxymethylideneamino derivative 7. Formic acid and malononitrile were reacted with compound 6d to produce thiazolo[3,2-a][1,8]naphthyridine derivative 8 and 11, respectively. Condensation of 2 with cyanoacetohydrazide in ethanol containing piperidine as catalyst gave the hydrazone derivative 12 which, on treatment with salicyaldehyde and 2-cyano-3-(4-fluorophenyl)acrylic acid ethyl ester, yielded the novel chromene 13 and pyridinone 14, respectively Structures of the synthesized compounds have been established by elemental analysis and spectral data. Compounds 3, 5, 6a-d, 8, 11, 13, and 14 have been screened for antimicrobial activities.

  DOI：

  10.1080/10426500490494778
• 作为产物：
  描述：

  1,3-噻唑啉-4-酮-2-乙腈 、 1,3-二苯-1H-吡唑-4-甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以75%的产率得到2-cyanomethyl-4,5-dihydro-4-oxo-5-(1,3-diphenylpyrazol-4-yl)methylidene thiazoline
  参考文献：
  名称：

  A Facile Synthesis of Some New Thiazolo[3, 2]pyridines Containing Pyrazolyl Moiety and Their Antimicrobial Activity

  摘要：

  Condensation of 2-cyanomethyl-4-thiazolinone 1 with 1,3-diphenyl-pyrozole-4-carboxaldehyde 2 in ethanol containing a few drops of piperidine yielded the novel methylene derivative 3. Compound 3 was refluxed with malononitrile to give the corresponding thiazolo[3,2-a]pyridine derivative 5. Also, treatment of compound 3 with benzylidenemalononitriles gave the thiazolo[3,2-a]pyridine derivatives 6a-e. Refluxing of compound 6d with triethyl orthoformate furnished the ethoxymethylideneamino derivative 7. Formic acid and malononitrile were reacted with compound 6d to produce thiazolo[3,2-a][1,8]naphthyridine derivative 8 and 11, respectively. Condensation of 2 with cyanoacetohydrazide in ethanol containing piperidine as catalyst gave the hydrazone derivative 12 which, on treatment with salicyaldehyde and 2-cyano-3-(4-fluorophenyl)acrylic acid ethyl ester, yielded the novel chromene 13 and pyridinone 14, respectively Structures of the synthesized compounds have been established by elemental analysis and spectral data. Compounds 3, 5, 6a-d, 8, 11, 13, and 14 have been screened for antimicrobial activities.

  DOI：

  10.1080/10426500490494778