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The synthesis of bicyclic 1,2,3,4-tetrahydro-1,4-benzodiazepin-5-ones from 2-(o-nitrobenzyl)-1,2-thiazine-1-oxide precursors

Hemming, Karl and Loukou, Christina (2004) The synthesis of bicyclic 1,2,3,4-tetrahydro-1,4-benzodiazepin-5-ones from 2-(o-nitrobenzyl)-1,2-thiazine-1-oxide precursors. Tetrahedron, 60. pp. 3349-3357. ISSN 0040-4020

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Abstract

Sulfinylation of o-nitrobenzamide and subsequent hetero Diels–Alder reaction gave a series of 2-(o-nitrobenzoyl)-1,2-thiazine-1-oxides. The 2-(o-nitrobenzoyl)-1,2-thiazine-1-oxides undergo a ring opening reaction with phenyl magnesium bromide to give allylic sulfoxides, which, after [2,3]-sigmatropic rearrangement and desulfurisation, furnish unsaturated vicinal N-(o-nitrobenzoyl)-1,2-amino alcohols. Oxidation of the alcohol and reductive ring closure gave a series of bicyclic 1,2,3,4-tetrahydro-1,4-benzodiazepin-5-ones, a subset of the ‘privileged’ 1,4-benzodiazepine structure. A 4-hydroxy-1,2,5-benzothiadiazepin-1,1-dioxide was synthesised by the same route starting from o-nitrobenzenesulfonamide.

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: 15 Sep 2010 12:25
URI: http://eprints.hud.ac.uk/id/eprint/244

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