Construction of functionalized tricyclic dihydropyrazino-quinazolinedione chemotypes via an Ugi/N-acyliminium ion cyclization cascade

Steven Gunawan, Christopher Hulme

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

Dihydropyrazino-quinazolinedione chemotypes are complex and structurally challenging structures of biological interest, being found in the marine alkaloids such as brevianamide M-N and fumiquinazolines A-C. Herein we report the synthesis of this tricyclic system in three synthetic operations by means of an Ugi multi-component reaction (MCR) followed by a tandem N-acyliminium ion cyclization-intramolecular nucleophilic addition reaction sequence. Additional structural diversification for further library enrichment was also accomplished via sequential N-alkylation and N-acylation/sulfonation.

Original languageEnglish (US)
Pages (from-to)4467-4470
Number of pages4
JournalTetrahedron Letters
Volume54
Issue number33
DOIs
StatePublished - Aug 14 2013

Keywords

  • Heterocycles
  • Multi-component reaction
  • N-acyliminium ion
  • Peptidomimetics
  • Ugi reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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