3-chloro-5-(N-methyl-1H-pyrrol-2-yl)-4H-1,2,6-thiadiazin-4-one | 1338699-71-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 3-chloro-5-(N-methyl-1H-pyrrol-2-yl)-4H-1,2,6-thiadiazin-4-one
• 英文别名: 3-chloro-5-(1-methyl-1H-pyrrol-2-yl)-4H-1,2,6-thiadiazin-4-one；3-Chloro-5-(1-methylpyrrol-2-yl)-1,2,6-thiadiazin-4-one；3-chloro-5-(1-methylpyrrol-2-yl)-1,2,6-thiadiazin-4-one
• CAS: 1338699-71-0
• 化学式: C₈H₆ClN₃OS
• 分子量: 227.674
• InChiKey: DEAQKLAJLLYLLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  72
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-5-(N-methyl-1H-pyrrol-2-yl)-4H-1,2,6-thiadiazin-4-one 、 2-(三丁基锡烷基)呋喃 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 乙腈 为溶剂， 反应 0.25h， 以94%的产率得到3-(fur-2-yl)-5-(1-methyl-1H-pyrrol-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
• 作为产物：
  描述：

  3-chloro-5-trifluoromethanesulfonoxy-4H-1,2,6-thiadiazin-4-one 、 N -甲基- 2 -(三正丁基锡)-的1H -吡咯 在 bis-triphenylphosphine-palladium(II) chloride 作用下， 以 苯 为溶剂， 反应 0.08h， 以94%的产率得到3-chloro-5-(N-methyl-1H-pyrrol-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