title: Efficient and divergent synthesis of fully substituted 1H-pyrazoles and isoxazoles from cyclopropyl oximes.
abstract: Efficient and divergent one-pot synthesis of fully substituted 1H-pyrazoles and isoxazoles from cyclopropyl oximes based on reaction conditions selection is reported. Under Vilsmeier conditions (POCl3/DMF), substituted 1 H-pyrazoles were synthesized from 1-carbamoyl, 1-oximyl cyclopropanes via sequential ring-opening, chlorovinylation, and intramolecular aza-cyclization. In the presence of POCl3/CH2Cl2, substituted isoxazoles were obtained from the cyclopropyl oximes via ring-opening and intramolecular nucleophilic vinylic substitution (SNV) reactions.
authors.affiliation: Department of Chemistry, Northeast Normal University, Changchun, China.
authors.forename: Kewei
authors.initials: K
authors.lastname: Wang
authors.forename: Dexuan
authors.initials: D
authors.lastname: Xiang
authors.forename: Jinying
authors.initials: J
authors.lastname: Liu
authors.forename: Wei
authors.initials: W
authors.lastname: Pan
authors.forename: Dewen
authors.initials: D
authors.lastname: Dong
mesh_terms: D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010091:Oximes / Q000737:chemistry*; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007555:Isoxazoles; D010091:Oximes; D011720:Pyrazoles