2-benzylsulfanylpyridinium-N-(4-chlorophenyl)imide | 569338-57-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-benzylsulfanylpyridinium-N-(4-chlorophenyl)imide
• 英文别名: (2-Benzylsulfanylpyridin-1-ium-1-yl)-(4-chlorophenyl)azanide
• CAS: 569338-57-4
• 化学式: C₁₈H₁₅ClN₂S
• 分子量: 326.849
• InChiKey: PGAHGQYACILTIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-benzylsulfanylpyridinium-N-(4-chlorophenyl)imide 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 5.0h， 生成 7-benzylsulfanyl-4-(4-chlorophenyl)-2-phenyl-1H-pyrrolo[3',4':4,5]-1H-pyrrolo[3,2-b]pyridine-1,3(2H)dione
  参考文献：
  名称：

  Unexpected Ring Transformation to Pyrrolo[3.2-b]pyridine Derivatives. Fused Azolium Salts. 22

  摘要：

  2-Arylsulfanyl and 2-benzylsulfanylpyridinium N-arylimides (2) easily prepared from 3-aryltetrazolopyridinium salts (1) with aryl and benzylthiolates, respectively, reacted with various dipolarophiles yielding cycloadducts that underwent transformation to give tetrahydropyrrolo[3,2-b]pyridines (5, 6, and 8) in good yields. A similar rearrangement (formation of 15) was also observed in the case of parent derivatives being unsubstituted in position 2 (12). The abscence of any significant solvent effect, comparison of the sulfur and non-sulfur analogues, as well as the stereoselective nature of the observed ring transformation seem to support a sigmatropic mechanism. Structure elucidation of the products has been carried out by single-crystal X-ray diffraction and H-1 NMR experiments.

  DOI：

  10.1021/jo034231a
• 作为产物：
  描述：

  benzylthiolate anion 、 3-(4-chlorophenyl)-3H-tetrazolo[1,5-a]pyridin-4-ium tetrafluoroborate 以85%的产率得到2-benzylsulfanylpyridinium-N-(4-chlorophenyl)imide
  参考文献：
  名称：

  Unexpected Ring Transformation to Pyrrolo[3.2-b]pyridine Derivatives. Fused Azolium Salts. 22

  摘要：

  2-Arylsulfanyl and 2-benzylsulfanylpyridinium N-arylimides (2) easily prepared from 3-aryltetrazolopyridinium salts (1) with aryl and benzylthiolates, respectively, reacted with various dipolarophiles yielding cycloadducts that underwent transformation to give tetrahydropyrrolo[3,2-b]pyridines (5, 6, and 8) in good yields. A similar rearrangement (formation of 15) was also observed in the case of parent derivatives being unsubstituted in position 2 (12). The abscence of any significant solvent effect, comparison of the sulfur and non-sulfur analogues, as well as the stereoselective nature of the observed ring transformation seem to support a sigmatropic mechanism. Structure elucidation of the products has been carried out by single-crystal X-ray diffraction and H-1 NMR experiments.

  DOI：

  10.1021/jo034231a

文献信息

• New Facile Tandem Route to Oxo- and Thioxo[1,2,4]triazolo[1,5-<i>a</i>]pyridinium Salts
  作者：Roberta Palkó、Zsuzsanna Riedl、Orsolya Egyed、László Fábián、György Hajós

  DOI：10.1021/jo061361l

  日期：2006.9.1

  5-b]pyridinium salts (1), participate in 1,3-dipolar cycloaddition with aryl isothiocyanates and aryl isocyanates to result in formation of fused thioxo- and oxo[1,2,4]triazolium salts (5 and 12), respectively. This transformation is interpreted as a regular 1,3-cycloaddition followed by spontaneous elimination of the aryl- or benzylsulfanyl group. Formation of these triazolium salts can be followedunder

  2-芳硫基吡啶基和苄基硫基吡啶鎓N-芳基酰亚胺（2），可轻松从四唑并[1,5- b ]吡啶鎓盐（1）中获得，与芳基异硫氰酸酯和芳基异氰酸酯一起参与1,3-偶极环加成反应，从而形成稠合的硫代[1,2,4]三唑鎓盐和氧代[1,2,4]三唑鎓盐（分别为5和12）。该转化被解释为常规的1，3-环加成，然后自发消除芳基-或苄基硫烷基。这些三唑鎓盐的形成可在适当的反应条件下通过开环反应进行，以提供一些新的三唑基烯基（6）。沿着路径1 → 5识别硫醇根阴离子的中间参与，使得可以简化一个简单的步骤至5，暗示串联反应序列。
• Formation of new pyridyl substituted enamines. Observation of a diaza-Cope rearrangement
  作者：Roberta Palkó、Orsolya Egyed、Petra Bombicz、Zsuzsanna Riedl、György Hajós

  DOI：10.1016/j.tet.2008.08.065

  日期：2008.11

  the starting pyridinium compound on the reagent, which is followed by a [3,3]-sigmatropic (‘diaza-Cope’) rearrangement. Ring opening of the pyrrolopyridine compounds by a base also yielded pyridylenamines, which proved to be positional isomers of the sigmatropic rearrangement products. The new pyridyl derivatives seem to be valuable compounds for further transformations. Thus, they can undergo thermal

  一些2-芳基硫代吡啶鎓酰亚胺与乙炔二甲酸二甲酯反应时表现出强烈的行为：发生1,3-偶极环化，然后进行环转化，生成吡咯并吡啶或5-吡啶基取代的烯胺以不同的方式形成。机理考虑表明，后一种不寻常的转变是通过在试剂上将起始吡啶鎓化合物的酰亚胺氮原子迈克尔加成而引发的，随后是[3,3]-σ（diaza-Cope）重排。吡咯并吡啶化合物通过碱的开环也产生了吡啶亚胺，其被证明是σ重排产物的位置异构体。新的吡啶基衍生物似乎是用于进一步转化的有价值的化合物。因此，