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John O'Shaughnessy, Desmond Cunningham, Paul Kavanagh, Dónal Leech, Patrick McArdle, Fawaz Aldabbagh
2004
November
Synlett
Synthesis of benzimidazolequinone analogue of cyclopropamitosene antitumor agents
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benzimidazoles bioreductive diazo-compounds heterocycles hydrazones BIOREDUCTIVE ANTICANCER AGENTS INDOLEQUINONES REDUCTION QUINONES DESIGN
2382
2384
The preparation of a pyrrolo[1,2-alpha]benzimidazole, pyrido[1,2-alpha]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-alpha]benzmidazolequinone was determined by cyclic voltammetry indicating single-electron reduction occurs more easily than mitomycin C or the cyclopropamitosenes.
https://www.thieme-connect.com/ejournals/abstract/10.1055/s-2004-831341
DOI 10.1055/s-2004-831341
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