(2R,3R,4R,10S,10aR)-rel-8-chloro-1,2,3,4,10,10a-hexahydro-2,10-ethenopyrimido[1,2-a]indole-3,4-dicarbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2R,3R,4R,10S,10aR)-rel-8-chloro-1,2,3,4,10,10a-hexahydro-2,10-ethenopyrimido[1,2-a]indole-3,4-dicarbonitrile
• 英文别名: (8R,11S,13S,14R,15R)-5-chloro-1,12-diazatetracyclo[9.2.2.02,7.08,13]pentadeca-2(7),3,5,9-tetraene-14,15-dicarbonitrile
• 化学式: C₁₅H₁₁ClN₄
• 分子量: 282.732
• InChiKey: PIUYGFNFWCSTJW-FWTMIXAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-p-Chlorphenyliminopyridiniumbetain 以 乙醚 、 甲苯 为溶剂， 反应 2.33h， 生成 (2R,3R,4R,10S,10aR)-rel-8-chloro-1,2,3,4,10,10a-hexahydro-2,10-ethenopyrimido[1,2-a]indole-3,4-dicarbonitrile
  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

• Unexpected Ring Transformation to Pyrrolo[3.2-<i>b</i>]pyridine Derivatives. Fused Azolium Salts. 22
  作者：Zsuzsanna Riedl、Péter Kövér、Tibor Soós、György Hajós、Orsolya Egyed、László Fábián、András Messmer

  DOI：10.1021/jo034231a

  日期：2003.7.1

  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.