Synthesis of benzimidazolequinone analogue of cyclopropamitosene antitumor agents

John O'Shaughnessy, Desmond Cunningham, Paul Kavanagh, Dónal Leech, Patrick McArdle, Fawaz Aldabbagh*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

The preparation of a pyrrolo[1,2-a]benzimidazole, pyrido[1,2-a] benzimidazole and pyrrolo[1,2-a]benzimidazolequinone containing a fused cyclopropane ring is reported. Their synthesis involved the thermolysis of the respective benzimidazole-2-Eschenmoser hydrazones (aziridinyl imines), which facilitated an intramolecular 1,3-dipolar cycloaddition. X-ray crystal structure of one [3+2] pyrazoline-cycloadduct is presented. The redox potential of -1.052 V (vs. ferrocene) for the cyclopropapyrrolo[1,2-o]benzimidazolequinone was determined by cyclic voltammetry indicating single-electron reduction occurs more easily than mitomycin C or the cyclopropamitosenes.

Original languageEnglish
Pages (from-to)2382-2384
Number of pages3
JournalSynlett
Issue number13
DOIs
Publication statusPublished - 03 Nov 2004
Externally publishedYes

Keywords

  • Benzimidazoles
  • Bioreductive
  • Diazo-compounds
  • Heterocycles
  • Hydrazones

ASJC Scopus subject areas

  • Organic Chemistry

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