title: Iodocyclization of hydroxylamine derivatives based on the control of oxidative aromatization leading to 2,5-dihydroisoxazoles and isoxazoles.
abstract: An efficient method for the synthesis of 2,5-dihydroisoxazoles and isoxazoles using iodocyclization of N-alkoxycarbonyl O-propargylic hydroxylamines has been developed. 2,5-Dihydro-4-iodoisoxazole underwent the cross-coupling reactions without aromatization to afford polyfunctionalized 2,5-dihydroisoxazoles. This process was applied to the preparation of valdecoxib and its 2,5-dihydro-derivative.
authors: Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, 4-19-1, Motoyamakita-machi, Kobe 658-8558, Japan.
authors: Takashi
authors: T
authors: Okitsu
authors: Kana
authors: K
authors: Sato
authors: Taterao M
authors: TM
authors: Potewar
authors: Akimori
authors: A
authors: Wada
mesh_terms: D003500:Cyclization; D006898:Hydroxylamines / Q000737:chemistry*; D007455:Iodine / Q000737:chemistry*; D007555:Isoxazoles / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D006898:Hydroxylamines; D007555:Isoxazoles; D007455:Iodine