N-allylthieno[2,3-b]pyridin-2-amine | 1224582-58-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: N-allylthieno[2,3-b]pyridin-2-amine
• 英文别名: N-prop-2-enylthieno[2,3-b]pyridin-2-amine
• CAS: 1224582-58-4
• 化学式: C₁₀H₁₀N₂S
• 分子量: 190.269
• InChiKey: HEFQVMYTPSFATQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-乙酰基-2-氯吡啶 、 丙烯胺 在 sodium acetate 、 sulfur 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 90.0 ℃ 、1.72 MPa 条件下， 反应 0.25h， 以66%的产率得到N-allylthieno[2,3-b]pyridin-2-amine
  参考文献：
  名称：

  Microwave-Assisted Synthesis of 3-Methylisothiazolo[5,4-b]pyridine and Various 2-Amino Derivatives of Thieno[2,3-b]pyridine and 1-(2-Aminopyridin-3-yl)ethanone

  摘要：

  Various 2-amino derivatives of thieno[2,3-b]pyridin-2-amine (3a-g) were prepared in fair to good yields (30-76%) by subjecting 1-(2-chloropyridin-3-yl)ethanone (1) and appropriate primary amine (2a-g) to microwave heating at 90-120 degrees C for 15-20 min in the presence of elemental sulfur, NaOAc, and DMF. Lower yields (4-15%) of the secondary 2-amino derivatives of 1-(pyridin-3-yl)ethanone product (4a-g) were also obtained. However, when the microwave-assisted reactions were carried out on primary (2b-h) and secondary amines (2i-o) in the absence of elemental S at 100-200 degrees C for 15-20 min, the respective secondary 2-amines (4b-h) and tertiary 2-amines (4i-o) of 1-(pyridin-3-yl)ethanones were obtained in good to excellent yields (61-98%). Finally, when 1 subjected to microwave heating at 120 degrees C for 15 min in the presence of elemental sulfur, NH(4)Cl, NaOAc, and DMF, 3-methyl-isothiazolo[5,4-b]pyridine (5) was obtained in 79% yield. Possible mechanisms for the formation of compounds 3-5 are presented.

  DOI：

  10.3987/com-09-s(s)119

文献信息

• Microwave-Assisted Synthesis of 3-Methylisothiazolo[5,4-b]pyridine and Various 2-Amino Derivatives of Thieno[2,3-b]pyridine and 1-(2-Aminopyridin-3-yl)ethanone
  作者：Edward R. Biehl、Haribabu Ankati

  DOI：10.3987/com-09-s(s)119

  日期：——

  Various 2-amino derivatives of thieno[2,3-b]pyridin-2-amine (3a-g) were prepared in fair to good yields (30-76%) by subjecting 1-(2-chloropyridin-3-yl)ethanone (1) and appropriate primary amine (2a-g) to microwave heating at 90-120 degrees C for 15-20 min in the presence of elemental sulfur, NaOAc, and DMF. Lower yields (4-15%) of the secondary 2-amino derivatives of 1-(pyridin-3-yl)ethanone product (4a-g) were also obtained. However, when the microwave-assisted reactions were carried out on primary (2b-h) and secondary amines (2i-o) in the absence of elemental S at 100-200 degrees C for 15-20 min, the respective secondary 2-amines (4b-h) and tertiary 2-amines (4i-o) of 1-(pyridin-3-yl)ethanones were obtained in good to excellent yields (61-98%). Finally, when 1 subjected to microwave heating at 120 degrees C for 15 min in the presence of elemental sulfur, NH(4)Cl, NaOAc, and DMF, 3-methyl-isothiazolo[5,4-b]pyridine (5) was obtained in 79% yield. Possible mechanisms for the formation of compounds 3-5 are presented.