Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines

0440479 - MBÚ 2015 RIV CH eng J - Článek v odborném periodiku
Hemming, K. - Chambers, Christopher S. - Jamshaid, F. - O´Gorman, Paul A.
Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines.
Molecules. Roč. 19, č. 10 (2014), s. 16737-16756. E-ISSN 1420-3049
Institucionální podpora: RVO:61388971
Klíčová slova: azide * cycloadditions * benzodiazepines
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 2.416, rok: 2014

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.
Trvalý link: http://hdl.handle.net/11104/0243582