Diverse Isoquinoline Scaffolds by Ugi/Pomeranz-Fritsch and Ugi/Schlittler-Müller Reactions

Yuanze Wang, Pravin Patil, Katarzyna Kurpiewska, Justyna Kalinowska-Tluscik, Alexander Dömling*

*Corresponding author for this work

Research output: Contribution to journalArticleAcademicpeer-review

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Abstract

The Pomeranz-Fritsch reaction and its Schlittler-Müller modification were successfully applied in the Ugi postcyclization strategy by using orthogonally protected aminoacetaldehyde diethyl acetal and complementary electron rich building blocks. Several scaffolds, including isoquinolines, carboline, alkaloid-like tetrazole-fused tetracyclic compounds, and benzo[ d]azepinone scaffolds, were synthesized in generally moderate to good yield. All our syntheses provide a short MCR-based sequence to novel or otherwise difficult to access scaffolds. Hence, we foresee multiple applications of these synthesis technologies.

Original languageEnglish
Pages (from-to)3533-3537
Number of pages5
JournalOrganic letters
Volume21
Issue number10
DOIs
Publication statusPublished - 17-May-2019

Keywords

  • SOLUTION-PHASE PREPARATION
  • PICTET-SPENGLER REACTION
  • ASYMMETRIC-SYNTHESIS
  • BOBBITT SYNTHESIS
  • UGI
  • ALKALOIDS
  • EFFICIENT
  • MCR
  • FUNCTIONALIZATION
  • QUINOLINES

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