Intramolecular azide to alkene cycloadditions for the construction of pyrrolobenzodiazepines and azetidino-benzodiazepines

Karl Hemming, Christopher S Chambers, Faisal Jamshaid, Paul A O'Gorman

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The coupling of proline- and azetidinone-substituted alkenes to 2-azidobenzoic and 2-azidobenzenesulfonic acid gives precursors that undergo intramolecular azide to alkene 1,3-dipolar cycloadditions to give imine-, triazoline- or aziridine-containing pyrrolo[1,4]benzodiazepines (PBDs), pyrrolo[1,2,5]benzothiadiazepines (PBTDs), and azetidino[1,4]benzodiazepines. The imines and aziridines are formed after loss of nitrogen from a triazoline cycloadduct. The PBDs are a potent class of antitumour antibiotics.

Original languageEnglish
Pages (from-to)16737-56
Number of pages20
JournalMolecules
Volume19
Issue number10
DOIs
Publication statusPublished - 2014

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