Rapid synthesis of hexahydropyrrolo[3,4-b]pyrrole-fused quinolinesviaa consecutive [3+2] cycloaddition and reduction/intramolecular lactamization cascade

Yan-Liang Lin, Yun-Ta Lee, Indrajeet J. Barve, Yi-Ting Huang, Chung-Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

An unprecedented synthesis of novel hexahydropyrrolo[3,4-b]pyrrole-fused quinolines is achieved through the sequential [3 + 2] cycloaddition reaction of azomethine ylides with maleimides followed by intramolecular lactamization. Condensation of the alpha-amino acid methyl ester with 2-nitrobenzaldehyde leads to an ester stabilized azomethine ylide which further reacts with maleimide to form hexahydropyrrolo[3,4-c]pyrrole. After the reduction of a nitro group, an unusual transamidation reaction is observed, furnishing the novel hexahydropyrrolo[3,4-b]pyrrole-fused quinolines. Isolation of the hexahydropyrrolo[3,4-c]pyrrole amide intermediate revealed the pathway of the reaction mechanism.

Original languageEnglish
Pages (from-to)2991-2996
Number of pages6
JournalOrganic Chemistry Frontiers
Volume7
Issue number19
DOIs
StatePublished - 7 Oct 2020

Keywords

  • DIASTEREOSELECTIVE SYNTHESIS
  • STEREOSELECTIVE-SYNTHESIS
  • SMALL MOLECULES

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