Photoassisted Diversity-Oriented Synthesis: Accessing 2,6-Epoxyazocane (Oxamorphan) Cores
نویسندگان
چکیده
The modular synthesis of photoprecursors and their photoinduced cyclization into substituted 1-benzazocanes of two distinct topologies is described. The key step producing an extended polyheterocyclic system involves the photogeneration of azaxylylenes and their subsequent intramolecular cycloaddition with furan-containing pendants tethered either via the aniline nitrogen or through the carbonyl group containing arm. The primary photoproducts-secondary or tertiary anilines which are not acylated at the nitrogen atom-undergo facile acid-catalyzed or spontaneous ring-opening-ring-closing rearrangement to yield fused polyheterocyclic structures possessing a 2,6-epoxyazocane (or oxamorphan) core.
منابع مشابه
Photoassisted synthesis of enantiopure alkaloid mimics possessing unprecedented polyheterocyclic cores.
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