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Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines
- Source :
- Molecules, Vol 19, Iss 10, Pp 16737-16756 (2014)
- Publication Year :
- 2014
- Publisher :
- MDPI AG, 2014.
-
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.
Details
- Language :
- English
- ISSN :
- 14203049
- Volume :
- 19
- Issue :
- 10
- Database :
- Directory of Open Access Journals
- Journal :
- Molecules
- Publication Type :
- Academic Journal
- Accession number :
- edsdoj.b643517331e349a7b7bce0df18e16769
- Document Type :
- article
- Full Text :
- https://doi.org/10.3390/molecules191016737