title: Amino Azaxylylenes Photogenerated from o-Amido Imines: Photoassisted Access to Complex Spiro-Poly-Heterocycles.
abstract: Upon irradiation, cyclic imines containing o-amido groups are shown to produce reactive intermediates, amino azaxylylenes, which undergo intramolecular cycloadditions to tethered unsaturated pendants to yield complex N,O-heterocycles having an additional spiro-connected nitrogen heterocyclic moiety. Modular assembly of the photoprecursors allows expeditious increase of the complexity of the target poly-heterocyclic scaffolds with a minimal number of experimentally simple reaction steps. The photocyclization and subsequent postphotochemical transformations are accompanied by an increase of Lovering's fsp3 factor, thus producing unprecedented three-dimensional molecular architectures, and offering extended sampling of chemical space.
authors.affiliation: Department of Chemistry and Biochemistry, University of Denver, 2190 E. Iliff Ave. Denver, CO 80208-2436 (USA) http://kgroup.du.edu.
authors.forename: Olga A
authors.initials: OA
authors.lastname: Mukhina
authors.affiliation: Department of Chemistry and Biochemistry, University of Denver, 2190 E. Iliff Ave. Denver, CO 80208-2436 (USA) http://kgroup.du.edu.
authors.forename: Dmitry M
authors.initials: DM
authors.lastname: Kuznetsov
authors.affiliation: Department of Chemistry and Biochemistry, University of Denver, 2190 E. Iliff Ave. Denver, CO 80208-2436 (USA) http://kgroup.du.edu.
authors.forename: Teresa M
authors.initials: TM
authors.lastname: Cowger
authors.affiliation: Department of Chemistry and Biochemistry, University of Denver, 2190 E. Iliff Ave. Denver, CO 80208-2436 (USA) http://kgroup.du.edu. akutatel@du.edu.
authors.forename: Andrei G
authors.initials: AG
authors.lastname: Kutateladze
mesh_terms: D003500:Cyclization; D006571:Heterocyclic Compounds / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D010777:Photochemistry; D014992:Xylenes / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D007097:Imines; D014992:Xylenes
keywords: cycloaddition; heterocycles; photochemistry; spiro compounds; synthetic methods