Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 11, Issue 9, Pages 2680-2688Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.200401112
Keywords
aza-Witticy reaction; benzodiazepines; heterocycles; solid-phase synthesis; traceless linker
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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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