(5R,6S,7S,7aS)-methyl 7-(phenylcarbamoyl)-7a-((1H-indol-3-yl)methyl)hexahydro-1-oxo-5-phenyl-3-thioxo-1H-pyrrolo[1,2-c]imidazole-6-carboxylate | 1349083-62-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (5R,6S,7S,7aS)-methyl 7-(phenylcarbamoyl)-7a-((1H-indol-3-yl)methyl)hexahydro-1-oxo-5-phenyl-3-thioxo-1H-pyrrolo[1,2-c]imidazole-6-carboxylate
• CAS: 1349083-62-0
• 化学式: C₃₀H₂₆N₄O₄S
• 分子量: 538.627
• InChiKey: AUXRPPQGYWYVFP-SODQHWRNSA-N

反应信息

• 作为产物：
  描述：

  ethyl 1-((1H-indol-3-yl)methyl)-2-((benzamido)carbothioyl)octahydro-4,6-dioxo-3,5-diphenylpyrrolo[3,4-c]pyrrole-1-carboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 36.0h， 以49%的产率得到(5R,6S,7S,7aS)-methyl 7-(phenylcarbamoyl)-7a-((1H-indol-3-yl)methyl)hexahydro-1-oxo-5-phenyl-3-thioxo-1H-pyrrolo[1,2-c]imidazole-6-carboxylate
  参考文献：
  名称：

  Polysubstituted Fused Ring Bicyclic Thiohydantoins from Aminocarbo-N-thioylpyrrolidines Derived from Azomethine Ylide 1,3-Dipolar Cycloadditions

  摘要：

  Highly substituted bicyclic thiohydantoins fused to pyrrolidines were prepared from aminocarbo-N-thioylpyrrolidines derived from alpha-amino acid esters via imine azomethine ylide 1,3-dipolar cycloadditions and subsequent reaction with aroylisothiocyanates. Aminocarbo-N-thioylpyrrolidines efficiently undergo cyclisation in the presence of sodium methoxide to form bicyclic N-substituted thiohydantoins with concomitant cleavage of the N-acyl group in good to excellent yield. And also some interesting both regiospecific and stereospecific rearrangement to the bicyclic fused thiocarbamoil pyrrolidine and bicyclic thiohydantoin were observed.

  DOI：

  10.3987/com-11-12276