5-(4-chlorophenyl)-3,4-dihydro-4-oxothieno[2,3-d]pyrimidine-6-carboxamide | 1374790-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 5-(4-chlorophenyl)-3,4-dihydro-4-oxothieno[2,3-d]pyrimidine-6-carboxamide
• 英文别名: 5-(4-chlorophenyl)-4-oxo-3H-thieno[2,3-d]pyrimidine-6-carboxamide
• CAS: 1374790-60-9
• 化学式: C₁₃H₈ClN₃O₂S
• 分子量: 305.744
• InChiKey: AYICYWDMKPRXRT-UHFFFAOYSA-N

物化性质

• 熔点：
  265-266 °C
• 沸点：
  512.0±60.0 °C(predicted)
• 密度：
  1.68±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  113
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-chlorophenyl)-3,4-dihydro-4-oxothieno[2,3-d]pyrimidine-6-carboxamide 在 五氯化磷 、 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 反应 2.5h， 生成 5-(4-chlorophenyl)-4-(piperazin-1-yl)thieno[2,3-d]pyrimidine-6-carbonitrile
  参考文献：
  名称：

  Synthetic tactics of new class of 4-aminothieno[2,3-d]pyrimidine-6-carbonitrile derivatives acting as antimicrobial agents

  摘要：

  Thermal selective reactions were studied on oxothieno[2,3-d]pyrimidine-6-carboxamide 3 with POCI3 and PCI5. At 25-50 degrees C, the C-7-amide rearranges to nitrile furnished compound 4 in 85-90% yield, while at 80-110 degrees C furnished mixture of products 4 and 5 in 28-68% yields. The chloro displacement with amines in compound 5 yielded 4-aminothieno[2,3-d]pyrimidine-6-carbonitrile derivatives 8(a h) and 9(a e). Antimicrobial activity of new compounds was studied against several bacteria such as Staphylococcus aureus MTCC-96, Escherichia coli MTCC-443, Pseudomonas aeruginosa MTCC-4 41, Streptococcus pyogenes MTCC-442 and fungi Aspergillus niger MTCC-282, Aspergillus clavatus MTCC-1323, Candida albicans MTCC-227 using broth microdilution method. Compounds 4, 8b, 8d, 8e, 8h and 9a showed promising antibacterial activity compared to ampicillin and compounds 8b, 8h showed better antifungal activity compared to greseofulvin. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.039
• 作为产物：
  描述：

  5-mino-3-(4-chlorophenyl)thiophene-2,4-dicarbonitrile 在 硫酸 、 水 作用下， 反应 11.0h， 生成 5-(4-chlorophenyl)-3,4-dihydro-4-oxothieno[2,3-d]pyrimidine-6-carboxamide
  参考文献：
  名称：

  Synthetic tactics of new class of 4-aminothieno[2,3-d]pyrimidine-6-carbonitrile derivatives acting as antimicrobial agents

  摘要：

  Thermal selective reactions were studied on oxothieno[2,3-d]pyrimidine-6-carboxamide 3 with POCI3 and PCI5. At 25-50 degrees C, the C-7-amide rearranges to nitrile furnished compound 4 in 85-90% yield, while at 80-110 degrees C furnished mixture of products 4 and 5 in 28-68% yields. The chloro displacement with amines in compound 5 yielded 4-aminothieno[2,3-d]pyrimidine-6-carbonitrile derivatives 8(a h) and 9(a e). Antimicrobial activity of new compounds was studied against several bacteria such as Staphylococcus aureus MTCC-96, Escherichia coli MTCC-443, Pseudomonas aeruginosa MTCC-4 41, Streptococcus pyogenes MTCC-442 and fungi Aspergillus niger MTCC-282, Aspergillus clavatus MTCC-1323, Candida albicans MTCC-227 using broth microdilution method. Compounds 4, 8b, 8d, 8e, 8h and 9a showed promising antibacterial activity compared to ampicillin and compounds 8b, 8h showed better antifungal activity compared to greseofulvin. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.039

文献信息

• Synthesis of new thieno[2,3-d]pyrimidines, thieno[3,2-e]pyridines, and thieno[2,3-d][1,3]oxazines
  作者：Shrikant B. Kanawade、Shivaraj P. Patil、Prashant S. Nikam、Sachin A. Gangurde、Madhukar N. Jachak、Raghunath B. Toche

  DOI：10.1002/jhet.748

  日期：2012.3

  o‐Aminothiophene dicarbonitrile 1 on neat reaction with cyclic ketones in anhydrous ZnCl2 yielded mixture of fused aminopyridine 3 and iminospirooxazine 4 derivatives. Similarly, pyrimidine derivatives 5 and 8 were obtained by the reaction of this intermediate 1 with formic acid and DMF‐DMA followed by hydrazine hydrate, respectively. The reaction of o‐amino‐thiophene dicarboxamide 2 at ambient temperature

  o-氨基噻吩二腈1与无水ZnCl 2中的环酮发生纯反应，可得到熔融的氨基吡啶3和亚氨基螺并恶嗪4衍生物的混合物。同样，嘧啶衍生物5和8是通过中间体1与甲酸和DMF-DMA分别与水合肼反应而获得的。的反应ø -氨基-噻吩二甲酰胺2在环境温度下与环酮，得到spiropyrimidine 10定量产率的鞋底制品。区域选择性芳基嘧啶9，通过分别在哌啶和碘的存在下与芳族醛反应，得到11，和二氢嘧啶12的衍生物。J.杂环化​​学。（2012）。
• Synthetic tactics of new class of 4-aminothieno[2,3-d]pyrimidine-6-carbonitrile derivatives acting as antimicrobial agents
  作者：Shrikant B. Kanawade、Raghunath B. Toche、Dhanji P. Rajani

  DOI：10.1016/j.ejmech.2013.03.039

  日期：2013.6

  Thermal selective reactions were studied on oxothieno[2,3-d]pyrimidine-6-carboxamide 3 with POCI3 and PCI5. At 25-50 degrees C, the C-7-amide rearranges to nitrile furnished compound 4 in 85-90% yield, while at 80-110 degrees C furnished mixture of products 4 and 5 in 28-68% yields. The chloro displacement with amines in compound 5 yielded 4-aminothieno[2,3-d]pyrimidine-6-carbonitrile derivatives 8(a h) and 9(a e). Antimicrobial activity of new compounds was studied against several bacteria such as Staphylococcus aureus MTCC-96, Escherichia coli MTCC-443, Pseudomonas aeruginosa MTCC-4 41, Streptococcus pyogenes MTCC-442 and fungi Aspergillus niger MTCC-282, Aspergillus clavatus MTCC-1323, Candida albicans MTCC-227 using broth microdilution method. Compounds 4, 8b, 8d, 8e, 8h and 9a showed promising antibacterial activity compared to ampicillin and compounds 8b, 8h showed better antifungal activity compared to greseofulvin. (C) 2013 Elsevier Masson SAS. All rights reserved.