6-(2,2'-bithiophen-5-yl)nicotinonitrile | 1268709-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 双噻吩和低聚噻吩
• 英文名称: 6-(2,2'-bithiophen-5-yl)nicotinonitrile
• 英文别名: 6-(5-thiophen-2-ylthiophen-2-yl)pyridine-3-carbonitrile
• CAS: 1268709-34-7
• 化学式: C₁₄H₈N₂S₂
• 分子量: 268.363
• InChiKey: ZTWVANWGNYBAJS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 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：
  93.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-(2,2'-bithiophen-5-yl)nicotinonitrile 在 sodium hydrogensulfite 、 三氯氧磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-[5'-(5-cyanopyridin-2-yl)-2,2'-bithiophen-5-yl]-1H-benzimidazole-6-carbonitrile
  参考文献：
  名称：

  Synthesis of Novel Bithiophene-Substituted Heterocycles Bearing Carbonitrile Groups

  摘要：

  Symmetrical and unsymmetrical bithiophene-substituted heterocycles bearing carbonitriles including imidazo[1,2-a]pyridine, benzimidazole, and pyridine derivatives have been synthesized via different synthetic protocols. The bithiophene bis-imidazo[1,2-a] pyridine derivatives 3a,b were achieved in three steps starting from 2-acetyl-5-bromothiophene. Suzuki coupling reaction of 2a with 5-formylthiophen-2-ylboronic acid forms the formyl derivative 5, which by condensation with 3,4-diaminobenzonitrile in the presence of sodium bisulfite furnishes the unsymmetrical bithiophene derivative6. The bis-benzimidazole derivative 8 was obtained via hexabutylditin-mediated homocoupling of 5-bromothiophene-2-carboxaldehyde, while the benzimidazole derivatives 12a,b were prepared via the formyl derivatives 11a,b, a product of Velsmier formylation reaction of 10a,b. Two synthetic protocols for the aryl/hetaryl-2,2'-bithiophene derivative 14 have also been presented. In addition, the guanyl hydrazones of bithiophenes, 16 and 17, were prepared from bis(tri-n-butylstannyl)-2,2'-bithiophene through a Stille coupling reaction followed by a condensation step.

  DOI：

  10.1080/00397910903537364
• 作为产物：
  描述：

  6-氯-3-氰基吡啶 、 2-(tri-n-butyl)stannyl-5,2'-bithiophene 在 四(三苯基膦)钯 作用下， 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以85%的产率得到6-(2,2'-bithiophen-5-yl)nicotinonitrile
  参考文献：
  名称：

  Synthesis of Novel Bithiophene-Substituted Heterocycles Bearing Carbonitrile Groups

  摘要：

  Symmetrical and unsymmetrical bithiophene-substituted heterocycles bearing carbonitriles including imidazo[1,2-a]pyridine, benzimidazole, and pyridine derivatives have been synthesized via different synthetic protocols. The bithiophene bis-imidazo[1,2-a] pyridine derivatives 3a,b were achieved in three steps starting from 2-acetyl-5-bromothiophene. Suzuki coupling reaction of 2a with 5-formylthiophen-2-ylboronic acid forms the formyl derivative 5, which by condensation with 3,4-diaminobenzonitrile in the presence of sodium bisulfite furnishes the unsymmetrical bithiophene derivative6. The bis-benzimidazole derivative 8 was obtained via hexabutylditin-mediated homocoupling of 5-bromothiophene-2-carboxaldehyde, while the benzimidazole derivatives 12a,b were prepared via the formyl derivatives 11a,b, a product of Velsmier formylation reaction of 10a,b. Two synthetic protocols for the aryl/hetaryl-2,2'-bithiophene derivative 14 have also been presented. In addition, the guanyl hydrazones of bithiophenes, 16 and 17, were prepared from bis(tri-n-butylstannyl)-2,2'-bithiophene through a Stille coupling reaction followed by a condensation step.

  DOI：

  10.1080/00397910903537364

文献信息

• Synthesis of Novel Bithiophene-Substituted Heterocycles Bearing Carbonitrile Groups
  作者：Mohamed A. Ismail、David W. Boykin

  DOI：10.1080/00397910903537364

  日期：2011.1.25

  Symmetrical and unsymmetrical bithiophene-substituted heterocycles bearing carbonitriles including imidazo[1,2-a]pyridine, benzimidazole, and pyridine derivatives have been synthesized via different synthetic protocols. The bithiophene bis-imidazo[1,2-a] pyridine derivatives 3a,b were achieved in three steps starting from 2-acetyl-5-bromothiophene. Suzuki coupling reaction of 2a with 5-formylthiophen-2-ylboronic acid forms the formyl derivative 5, which by condensation with 3,4-diaminobenzonitrile in the presence of sodium bisulfite furnishes the unsymmetrical bithiophene derivative6. The bis-benzimidazole derivative 8 was obtained via hexabutylditin-mediated homocoupling of 5-bromothiophene-2-carboxaldehyde, while the benzimidazole derivatives 12a,b were prepared via the formyl derivatives 11a,b, a product of Velsmier formylation reaction of 10a,b. Two synthetic protocols for the aryl/hetaryl-2,2'-bithiophene derivative 14 have also been presented. In addition, the guanyl hydrazones of bithiophenes, 16 and 17, were prepared from bis(tri-n-butylstannyl)-2,2'-bithiophene through a Stille coupling reaction followed by a condensation step.