Efficient solid-phase synthesis of highly functionalized 1,4-benzodiazepin-5-one derivatives and related compounds by intramolecular aza-Wittig reactions

Gil, C; Brase, S

Abstract

Due to their widespread biological activities and favorable pharmacokinetic properties, benzodiazepines were among the first classes of small molecules to be synthesized on solid supports. Since then, there have been numerous reports on the synthesis of similar skeletons. We have employed the T1 triazene linker to yield 1,4-benzodiazepin-5-one. Starting from various substituted triazene resins, cleavage in the presence of an azide donor, such as trimethylsilylazide, gave rise to aryl azides. Intramolecular aza-Wittig reactions produced the appropriately functionalized N-heterocycles. By using this route, the natural product deoxyvasicinone and related compounds were prepared.

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Título según WOS: ID WOS:000228757000008 Not found in local WOS DB
Título de la Revista: CHEMISTRY-A EUROPEAN JOURNAL
Volumen: 11
Número: 9
Editorial: WILEY-V C H VERLAG GMBH
Fecha de publicación: 2005
Página de inicio: 2680
Página final: 2688
DOI:

10.1002/chem.200401112

Notas: ISI