The synthesis of pyrrolo[1,2,b][1,2,5]benzothiadiazepines from 1,2-thiazine 1-oxides-sulfonamide analogues of the pyrrolobenzodiazepine antitumour natural products

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Hemming, Karl and Patel, N. (2004) The synthesis of pyrrolo[1,2,b][1,2,5]benzothiadiazepines from 1,2-thiazine 1-oxides-sulfonamide analogues of the pyrrolobenzodiazepine antitumour natural products. Tetrahedron Letters, 45. pp. 7553-7556. ISSN 0040-4039

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Official URL: http://dx.doi.org/10.1016/j.tetlet.2004.08.136

DOI: 10.1016/j.tetlet.2004.08.136

Abstract

Pyrrolo[2,1-c][1,4]benzodiazepines (PBDs) and the corresponding pyrrolobenzothiadiazepines (PBTDs) are attractive targets as natural and synthetic antitumour antibiotics and as non-nucleosidic reverse transcriptase inhibitors. A concise synthesis of the PBTD class is presented, which starts from o-azidobenzenesulfonamide and its conversion into 2-(o-azidobenzenesulfonyl)-1,2-thiazine 1-oxides via Diels–Alder reaction. After a one-pot ring contraction, desulfurisation and aromatisation process, accompanied by concomitant same pot conversion of the azide group into a primary amine via the Staudinger reaction, these 1,2-thiazine-1-oxides yield a 1-(o-aminobenzenesulfonyl)pyrrole. N-Formylation of the amine and Bischler–Napieralski ring closure onto the pyrrole completes the PBTD synthesis.

Item Type:	Article
Additional Information:	Copyright © 2007 Elsevier B.V. All rights reserved. ScienceDirect® is a registered trademark of Elsevier B.V.
Subjects:	Q Science > QD Chemistry
Schools:	School of Applied Sciences School of Applied Sciences > Biomolecular Sciences Research Centre
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Depositing User:	Briony Heyhoe
Date Deposited:	13 Jul 2007
Last Modified:	28 Jul 2010 19:20
URI:	http://eprints.hud.ac.uk/id/eprint/239

The synthesis of pyrrolo[1,2,b][1,2,5]benzothiadiazepines from 1,2-thiazine 1-oxides-sulfonamide analogues of the pyrrolobenzodiazepine antitumour natural products

Abstract

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