3-(1-methyl-1H-pyrrol-2-yl)-5-(thien-2-yl)-4H-1,2,6-thiadiazin-4-one | 1338699-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 3-(1-methyl-1H-pyrrol-2-yl)-5-(thien-2-yl)-4H-1,2,6-thiadiazin-4-one
• 英文别名: 3-(1-Methylpyrrol-2-yl)-5-thiophen-2-yl-1,2,6-thiadiazin-4-one；3-(1-methylpyrrol-2-yl)-5-thiophen-2-yl-1,2,6-thiadiazin-4-one
• CAS: 1338699-79-8
• 化学式: C₁₂H₉N₃OS₂
• 分子量: 275.355
• InChiKey: IGGMKFXEKCZSCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N -甲基- 2 -(三正丁基锡)-的1H -吡咯 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 乙腈 、 苯 为溶剂， 反应 0.83h， 生成 3-(1-methyl-1H-pyrrol-2-yl)-5-(thien-2-yl)-4H-1,2,6-thiadiazin-4-one
  参考文献：
  名称：

  Selective Stille Coupling Reactions of 3-Chloro-5-halo(pseudohalo)-4H-1,2,6-thiadiazin-4-ones

  摘要：

  A series of 3-chloro-5-halo(pseudohalo)-4H-1,2,6-thiadiazin-4-ones (halo/pseudohalo = Br, I, OTf) are prepared from 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (3) in good yields. Of these the triflate reacts with tributyltin arenes (Stille couplings) chemoselectively to give only the 5-aryl-3-chloro-4H-1,2,6-thiadiazin-4-ones in high yields. This allowed the preparation of a series of unsymmetrical biaryl thiadiazines and ultimately a series of oligomers. Furthermore, treatment of 3-chloro-5-iodo-4H-1,2,6-thiadiazin-4-one (10) with Bu3SnH and Pd(OAc)(2) gave the bithiadiazinone which can also be further arylated via the Stille reaction to give bisthien-2-yl and bis(N-methylpyrrol-2-yl) analogs.

  DOI：

  10.1021/ol2025235

文献信息

• Selective Stille Coupling Reactions of 3-Chloro-5-halo(pseudohalo)-4<i>H</i>-1,2,6-thiadiazin-4-ones
  作者：Heraklidia A. Ioannidou、Christos Kizas、Panayiotis A. Koutentis

  DOI：10.1021/ol2025235

  日期：2011.11.4

  A series of 3-chloro-5-halo(pseudohalo)-4H-1,2,6-thiadiazin-4-ones (halo/pseudohalo = Br, I, OTf) are prepared from 3,5-dichloro-4H-1,2,6-thiadiazin-4-one (3) in good yields. Of these the triflate reacts with tributyltin arenes (Stille couplings) chemoselectively to give only the 5-aryl-3-chloro-4H-1,2,6-thiadiazin-4-ones in high yields. This allowed the preparation of a series of unsymmetrical biaryl thiadiazines and ultimately a series of oligomers. Furthermore, treatment of 3-chloro-5-iodo-4H-1,2,6-thiadiazin-4-one (10) with Bu3SnH and Pd(OAc)(2) gave the bithiadiazinone which can also be further arylated via the Stille reaction to give bisthien-2-yl and bis(N-methylpyrrol-2-yl) analogs.