Synthesis of benzoxazolones from nitroarenes or aryl halides.
A simple and effective method for the preparation of benzoxazolones from nitroarenes or aryl halides is described. Partial reduction of a nitro group in the presence of a chloroformate followed by a microwave-assisted rearrangement/ring closure sequence provides a convenient and practical procedure to prepare this important pharmacophore. Rearrangement precursors were also accessed from aryl halides through transition-metal-catalyzed coupling.
Porzelle
Achim
A
School of Chemistry, Main Building, Cardiff University, UK.
Woodrow
Michael D
MD
Tomkinson
Nicholas C O
NC
D001583:Benzoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*
D001583:Benzoxazoles; D006846:Hydrocarbons, Halogenated; D009574:Nitro Compounds; C017057:benzoxazolone