5,5'-bis(1-methyl-1H-pyrrol-2-yl)-4H,4'H-[3,3'-bi(1,2,6-thiadiazine)]-4,4'-dione | 1338699-77-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5,5'-bis(1-methyl-1H-pyrrol-2-yl)-4H,4'H-[3,3'-bi(1,2,6-thiadiazine)]-4,4'-dione
• 英文别名: 5,5'-di(1-methyl-1H-pyrrol-2-yl)-4H,4'H-[3,3'-bi(1,2,6-thiadiazine)]-4,4'-dione；3-(1-Methylpyrrol-2-yl)-5-[5-(1-methylpyrrol-2-yl)-4-oxo-1,2,6-thiadiazin-3-yl]-1,2,6-thiadiazin-4-one；3-(1-methylpyrrol-2-yl)-5-[5-(1-methylpyrrol-2-yl)-4-oxo-1,2,6-thiadiazin-3-yl]-1,2,6-thiadiazin-4-one
• CAS: 1338699-77-6
• 化学式: C₁₆H₁₂N₆O₂S₂
• 分子量: 384.442
• InChiKey: CMTPAKRVHJPVTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5,5'-dichloro-4H,4'H-[3,3'-bi(1,2,6-thiadiazine)]-4,4'-dione 、 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 为溶剂， 反应 5.0h， 以70%的产率得到5,5'-bis(1-methyl-1H-pyrrol-2-yl)-4H,4'H-[3,3'-bi(1,2,6-thiadiazine)]-4,4'-dione
  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