4-(4-methoxyphenyl)-2-(methylthio)-6-(2-thienyl)-nicotinonitrile | 329720-96-9

• 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: 4-(4-methoxyphenyl)-2-(methylthio)-6-(2-thienyl)-nicotinonitrile
• 英文别名: 4-(4-Methoxyphenyl)-2-(methylsulfanyl)-6-(2-thienyl)nicotinonitrile；4-(4-methoxyphenyl)-2-methylsulfanyl-6-thiophen-2-ylpyridine-3-carbonitrile
• CAS: 329720-96-9
• 化学式: C₁₈H₁₄N₂OS₂
• 分子量: 338.454
• InChiKey: UPILETBJBCYAMR-UHFFFAOYSA-N

物化性质

• 熔点：
  192 °C(Solv: chloroform (67-66-3))
• 沸点：
  516.3±50.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-methoxyphenyl)-2-(methylthio)-6-(2-thienyl)-nicotinonitrile 在 吡啶 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以81%的产率得到4-(4-methoxyphenyl)-6-(2-thienyl)-1H-pyrazolo[3,4-b]pyridin-3-amine
  参考文献：
  名称：

  Synthesis of Heterocycles via 2-Thioxo-1,2-dihydropyridine-3-carbonitrile Derivative

  摘要：

  The present study aimed to investigate the synthetic potentiality and chemical reactivity of 2-thioxo-1,2-dihydropyridine-3-carbonitrile derivative 1. This goal performed via its reaction with each of 1-chloroacetone and iodomethane to afford the corresponding 2-alkylthio derivatives 3 and 9, respectively. Compound 3 underwent intramolecular cyclization to afford the corresponding thieno[2,3-b]pyridine derivative 4 which in turn, reacted with dimethylformamide/dimethylacetal followed by hydrazine hydrate and nitrous acid to afford the corresponding pyridothienopyrimidine and pyridothienopyridazine derivatives 6 and 8, respectively. On the other hand, Compound 9 reacted with hydrazine hydrate to give 3-aminopyrazolo[3,4-b]pyridine derivative 10, which diazotized with nitrous acid to give the corresponding diazonium salt 11. Compound 11 coupled with several active -CH2- containing reagents to synthesize the corresponding pyridopyrazolo-triazines 15, 24, 29, and 31. The formulas of all newly synthesized heterocyclic compounds were elucidated by considering the data of IR, H-1 NMR, Mass spectral data, as well as data from elemental analyses.

  DOI：

  10.1080/10426500801963905
• 作为产物：
  描述：

  4-(4-methoxyphenyl)-6-(thiophen-2-yl)-2-thioxo-1,2-dihydropyridine-3-carbonitrile 、 碘甲烷 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以90%的产率得到4-(4-methoxyphenyl)-2-(methylthio)-6-(2-thienyl)-nicotinonitrile
  参考文献：
  名称：

  Synthesis of Heterocycles via 2-Thioxo-1,2-dihydropyridine-3-carbonitrile Derivative

  摘要：

  The present study aimed to investigate the synthetic potentiality and chemical reactivity of 2-thioxo-1,2-dihydropyridine-3-carbonitrile derivative 1. This goal performed via its reaction with each of 1-chloroacetone and iodomethane to afford the corresponding 2-alkylthio derivatives 3 and 9, respectively. Compound 3 underwent intramolecular cyclization to afford the corresponding thieno[2,3-b]pyridine derivative 4 which in turn, reacted with dimethylformamide/dimethylacetal followed by hydrazine hydrate and nitrous acid to afford the corresponding pyridothienopyrimidine and pyridothienopyridazine derivatives 6 and 8, respectively. On the other hand, Compound 9 reacted with hydrazine hydrate to give 3-aminopyrazolo[3,4-b]pyridine derivative 10, which diazotized with nitrous acid to give the corresponding diazonium salt 11. Compound 11 coupled with several active -CH2- containing reagents to synthesize the corresponding pyridopyrazolo-triazines 15, 24, 29, and 31. The formulas of all newly synthesized heterocyclic compounds were elucidated by considering the data of IR, H-1 NMR, Mass spectral data, as well as data from elemental analyses.

  DOI：

  10.1080/10426500801963905

文献信息

• Synthesis of Heterocycles via 2-Thioxo-1,2-dihydropyridine-3-carbonitrile Derivative
  作者：Azza M. Abdel-Fattah、Labeeb M. Shaif、Fawzy A. Attaby

  DOI：10.1080/10426500801963905

  日期：2008.9.15

  The present study aimed to investigate the synthetic potentiality and chemical reactivity of 2-thioxo-1,2-dihydropyridine-3-carbonitrile derivative 1. This goal performed via its reaction with each of 1-chloroacetone and iodomethane to afford the corresponding 2-alkylthio derivatives 3 and 9, respectively. Compound 3 underwent intramolecular cyclization to afford the corresponding thieno[2,3-b]pyridine derivative 4 which in turn, reacted with dimethylformamide/dimethylacetal followed by hydrazine hydrate and nitrous acid to afford the corresponding pyridothienopyrimidine and pyridothienopyridazine derivatives 6 and 8, respectively. On the other hand, Compound 9 reacted with hydrazine hydrate to give 3-aminopyrazolo[3,4-b]pyridine derivative 10, which diazotized with nitrous acid to give the corresponding diazonium salt 11. Compound 11 coupled with several active -CH2- containing reagents to synthesize the corresponding pyridopyrazolo-triazines 15, 24, 29, and 31. The formulas of all newly synthesized heterocyclic compounds were elucidated by considering the data of IR, H-1 NMR, Mass spectral data, as well as data from elemental analyses.