title: Photoassisted diversity-oriented synthesis: accessing 2,6-epoxyazocane (oxamorphan) cores.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Denver , Denver, Colorado 80208, United States.
authors.forename: Olga A
authors.initials: OA
authors.lastname: Mukhina
authors.forename: N N Bhuvan
authors.initials: NN
authors.lastname: Kumar
authors.forename: Teresa M
authors.initials: TM
authors.lastname: Cowger
authors.forename: Andrei G
authors.initials: AG
authors.lastname: Kutateladze
mesh_terms: D061565:Cycloaddition Reaction; D003508:Cycloheptanes / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D055668:Photochemical Processes; D013237:Stereoisomerism
chemical_list: C000599345:2,6-epoxyazocane; D003508:Cycloheptanes; D006571:Heterocyclic Compounds