Efficient Solid‐Phase Synthesis of Highly Functionalized 1,4‐Benzodiazepin‐5‐one Derivatives and Related Compounds by Intramolecular Aza–Wittig Reactions
- 15 April 2005
- journal article
- Published by Wiley in Chemistry – A European Journal
- Vol. 11 (9) , 2680-2688
- https://doi.org/10.1002/chem.200401112
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.Keywords
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