One-pot Synthesis of Isoquinoline-Fused Isoquinolines via Intramolecular Hydroamination/Aza-Claisen Type Rearrangement Cascade

Wei Jung Chiu, Jin Yu Chen, Shih I. Liu, Indrajeet J. Barve, Wan Wen Huang, Chung Ming Sun*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract

A one-pot, two-step synthesis of isoquinoline-fused isoquinolines from α-amino acid esters and 2-alkynyl benzaldehydes are reported. The strategy comprises an unconventional Pictet-Spengler reaction between α-amino acid esters and 2-alkynyl benzaldehydes to give isoquinoline intermediates. Subsequent gold-catalyzed intramolecular hydroamination furnishes isoquinoline-fused isoquinolines. The scope of this strategy is further extended to prepare multisubstituted isoquinoline-fused isoquinolines via subjecting the N-allylated isoquinoline intermediates to gold-catalyzed intramolecular hydroamination followed by aza-Claisen type rearrangement. (Figure presented.).

Original languageEnglish
JournalAdvanced Synthesis and Catalysis
DOIs
StateAccepted/In press - 2021

Keywords

  • aza claisen-type rearrangement
  • hydroaminati-on
  • isoquinoline-fused isoquinolines

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