title: Heterocycle-heterocycle strategies: (2-nitrophenyl)isoxazole precursors to 4-aminoquinolines, 1H-indoles, and quinolin-4(1H)-ones.
abstract: Reductive heterocycle-heterocycle (heterocycle → heterocycle; H-H) transformations that give 4-aminoquinolines, 3-acylindoles, and quinolin-4(1H)-ones from 2-nitrophenyl substituted isoxazoles are reported. When this methodology is applied to 3,5-, 4,5-, and 3,4-bis(2-nitrophenyl)isoxazoles, chemoselective heterocyclization gives quinolin-4(1H)-ones, and 4-aminoquinolines, exclusively.
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, United States.
authors.forename: Keith C
authors.initials: KC
authors.lastname: Coffman
authors.forename: Teresa A
authors.initials: TA
authors.lastname: Palazzo
authors.forename: Timothy P
authors.initials: TP
authors.lastname: Hartley
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.forename: Dean J
authors.initials: DJ
authors.lastname: Tantillo
authors.forename: Mark J
authors.initials: MJ
authors.lastname: Kurth
mesh_terms: D000634:Aminoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000737:chemistry*; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000634:Aminoquinolines; D007211:Indoles; D007555:Isoxazoles; D015363:Quinolones; C001920:4-aminoquinoline
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