title: [3 + 2] Cycloaddition/Oxidative Aromatization Sequence via Photoredox Catalysis: One-Pot Synthesis of Oxazoles from 2H-Azirines and Aldehydes.
abstract: A novel [3 + 2] cycloaddition/oxidative aromatization sequence via visible light-induced photoredox catalysis is disclosed. It provides a general synthetic route to 2,4,5-trisubstituted oxazoles from easily accessible 2H-azirines and aldehydes under mild reaction conditions. The potential of this strategy was further demonstrated by the rapid synthesis of a cyclooxygenase-2 inhibitor as well as the success of employing electron-deficient alkenes and imines as the reaction partners.
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China.
authors.forename: Ting-Ting
authors.initials: TT
authors.lastname: Zeng
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China.
authors.forename: Jun
authors.initials: J
authors.lastname: Xuan
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China.
authors.forename: Wei
authors.initials: W
authors.lastname: Ding
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China.
authors.forename: Kuan
authors.initials: K
authors.lastname: Wang
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China.
authors.forename: Liang-Qiu
authors.initials: LQ
authors.lastname: Lu
authors.affiliation: Key Laboratory of Pesticide and Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, China.
authors.forename: Wen-Jing
authors.initials: WJ
authors.lastname: Xiao
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D001389:Azirines / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D052246:Cyclooxygenase 2 Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007097:Imines / Q000737:chemistry; D008027:Light; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction
chemical_list: D000447:Aldehydes; D000475:Alkenes; D001389:Azirines; D052246:Cyclooxygenase 2 Inhibitors; D007097:Imines; D010080:Oxazoles