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

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

doi:10.3390/molecules191016737

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 journal › Article › peer-review

15 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 language	English
Pages (from-to)	16737-16756
Number of pages	20
Journal	Molecules
Volume	19
Issue number	10
DOIs	https://doi.org/10.3390/molecules191016737
Publication status	Published - 17 Oct 2014

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10.3390/molecules191016737Licence: CC BY

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AU - O'Gorman, Paul A

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

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Karl Hemming

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

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Karl Hemming

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