title: Facile synthesis of disubstituted isoxazoles from homopropargylic alcohol via C═N bond formation.
abstract: A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, t-BuONO, and H2O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a C═N bond and C═O bond, C-H oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University , Lanzhou 730000, P. R. China.
authors.forename: Pin
authors.initials: P
authors.lastname: Gao
authors.forename: Hong-Xia
authors.initials: HX
authors.lastname: Li
authors.forename: Xin-Hua
authors.initials: XH
authors.lastname: Hao
authors.forename: Dong-Po
authors.initials: DP
authors.lastname: Jin
authors.forename: Dao-Qian
authors.initials: DQ
authors.lastname: Chen
authors.forename: Xiao-Biao
authors.initials: XB
authors.lastname: Yan
authors.forename: Xin-Xing
authors.initials: XX
authors.lastname: Wu
authors.forename: Xian-Rong
authors.initials: XR
authors.lastname: Song
authors.forename: Xue-Yuan
authors.initials: XY
authors.lastname: Liu
authors.forename: Yong-Min
authors.initials: YM
authors.lastname: Liang
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006860:Hydrogen Bonding; D007501:Iron / Q000737:chemistry; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D007555:Isoxazoles; D007501:Iron