(5R,6R,7aR)-methyl 7a-benzyl-hexahydro-1-oxo-5-(pyridin-3-yl)-3-thioxo-1H-pyrrolo[1,2-c]imidazole-6-carboxylate | 1349083-60-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: (5R,6R,7aR)-methyl 7a-benzyl-hexahydro-1-oxo-5-(pyridin-3-yl)-3-thioxo-1H-pyrrolo[1,2-c]imidazole-6-carboxylate
• CAS: 1349083-60-8
• 化学式: C₂₀H₁₉N₃O₃S
• 分子量: 381.455
• InChiKey: GIWSKZAAIFTSRZ-GUXCAODWSA-N

反应信息

• 作为产物：
  描述：

  dimethyl 1-((benzamido)carbothioyl)-2-benzyl-5-(pyridin-3-yl)pyrrolidine-2,4-dicarboxylate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 (5R,6S,7aR)-methyl 7a-benzyl-hexahydro-1-oxo-5-(pyridin-3-yl)-3-thioxo-1H-pyrrolo[1,2-c]imidazole-6-carboxylate 、 (5R,6R,7aR)-methyl 7a-benzyl-hexahydro-1-oxo-5-(pyridin-3-yl)-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