title: Intramolecular azide to alkene cycloadditions for the construction of pyrrolobenzodiazepines and azetidino-benzodiazepines.
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.
authors.affiliation: Department of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield, West Yorkshire HD1 3DH, UK. k.hemming@hud.ac.uk.
authors.forename: Karl
authors.initials: K
authors.lastname: Hemming
authors.affiliation: Department of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield, West Yorkshire HD1 3DH, UK.
authors.forename: Christopher S
authors.initials: CS
authors.lastname: Chambers
authors.affiliation: Department of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield, West Yorkshire HD1 3DH, UK.
authors.forename: Faisal
authors.initials: F
authors.lastname: Jamshaid
authors.affiliation: Department of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield, West Yorkshire HD1 3DH, UK.
authors.forename: Paul A
authors.initials: PA
authors.lastname: O'Gorman
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000903:Antibiotics, Antineoplastic / Q000138:chemical synthesis*; D001386:Azides / Q000737:chemistry*; D001569:Benzodiazepines / Q000138:chemical synthesis*; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis*
chemical_list: D000475:Alkenes; D000903:Antibiotics, Antineoplastic; D001386:Azides; D011758:Pyrroles; C438462:pyrrolo(2,1-c)(1,4)benzodiazepine; D001569:Benzodiazepines