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Molecules 2014, 19(10), 16737-16756; doi:10.3390/molecules191016737

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

1
Department of Chemical Sciences, University of Huddersfield, Queensgate, Huddersfield, West Yorkshire HD1 3DH, UK
2
Laboratory of Biotransformation, Institute of Microbiology, Academy of Sciences of Czech Republic, Vídeňská 1083, Praha 4, 142 20, Czech Republic
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 31 July 2014 / Revised: 26 September 2014 / Accepted: 13 October 2014 / Published: 17 October 2014
(This article belongs to the Special Issue Cycloaddition Chemistry)
View Full-Text   |   Download PDF [378 KB, uploaded 17 October 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. View Full-Text
Keywords: cycloaddition; 1,3-dipole; azide; pyrrolobenzodiazepine; azetidinone; antitumour; antibiotic; β-lactam cycloaddition; 1,3-dipole; azide; pyrrolobenzodiazepine; azetidinone; antitumour; antibiotic; β-lactam
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Hemming, K.; Chambers, C.S.; Jamshaid, F.; O'Gorman, P.A. Intramolecular Azide to Alkene Cycloadditions for the Construction of Pyrrolobenzodiazepines and Azetidino-Benzodiazepines. Molecules 2014, 19, 16737-16756.

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