Photoassisted Synthesis of Complex Molecular Architectures: Dearomatization of Benzenoid Arenes with Aza-o-xylylenes via an Unprecedented [2+4] Reaction Topology.
A new method was developed for the photoinduced dearomatization of arenes through an intramolecular cycloaddition with aza-o-xylylenes generated by excited-state intramolecular proton transfer (ESIPT) in the readily available photoprecursors. The [2+4] topology of this cycloaddition is unprecedented for photo-dearomatizations of benzenoid aromatic carbocycles. It provides rapid access to novel heterocycles, cyclohexadieno-oxazolidino-quinolinols, as valuable synthons for a broad range of post-photochemical transformations.
Department of Chemistry and Biochemistry, University of Denver, 2190 E. Iliff Ave., Denver, CO, 80208, USA.
Dmitry M
DM
Kuznetsov
Department of Chemistry and Biochemistry, University of Denver, 2190 E. Iliff Ave., Denver, CO, 80208, USA.
Olga A
OA
Mukhina
Department of Chemistry and Biochemistry, University of Denver, 2190 E. Iliff Ave., Denver, CO, 80208, USA. akutatel@du.edu.
Andrei G
0000-0003-3066-517X
AG
Kutateladze
D001372:Aza Compounds / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D061565:Cycloaddition Reaction; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D006912:Hydroxyquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D055668:Photochemical Processes; D013237:Stereoisomerism; D014992:Xylenes / Q000737:chemistry*
D001372:Aza Compounds; D001555:Benzene Derivatives; D006571:Heterocyclic Compounds; D006912:Hydroxyquinolines; D014992:Xylenes
[2+4] reactions; aza-o-xylylenes; dearomatization; photochemistry; polyheterocycles