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

Karl Hemming, Christina Loukou

Research output: Contribution to journalArticle

23 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)3349-3357
Number of pages9
JournalTetrahedron
Volume60
Issue number15
Early online date19 Mar 2004
DOIs
Publication statusPublished - 5 Apr 2004

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Thiazines
Oxides
Sulfoxides
Amino Alcohols
Cycloaddition Reaction
Alcohols
Oxidation
tetrahydro-1,4-benzodiazepin-2-one

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The synthesis of bicyclic 1,2,3,4-tetrahydro-1,4-benzodiazepin-5-ones from 2-(o-nitrobenzoyl)-1,2-thiazine-1-oxide precursors. / Hemming, Karl; Loukou, Christina.

In: Tetrahedron, Vol. 60, No. 15, 05.04.2004, p. 3349-3357.

Research output: Contribution to journalArticle

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