title: Heterocycle-to-Heterocycle Route to Quinoline-4-amines: Reductive Heterocyclization of 3-(2-Nitrophenyl)isoxazoles.
abstract: A variety of quinoline-4-amines were synthesized from substituted 3-(2-nitrophenyl)isoxazoles utilizing Zn0or Fe0dust and HOAc via a reductive heterocyclization process. The starting isoxazoles were synthesized from readily available starting materials. A brief survey of functional groups tolerated in this reductive heterocyclization was performed and several 10-amino-3,4-dihydrobenzo[b][1,6]naphthyridin-1(2H)-one and 9-amino-3,4-dihydroacridin-1(2H)-one examples were synthesized.
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, http://chemistry.ucdavis.edu/faculty/department_faculty/mark_kurth.html.
authors.forename: Keith C
authors.initials: KC
authors.lastname: Coffman
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, http://chemistry.ucdavis.edu/faculty/department_faculty/mark_kurth.html.
authors.forename: Vy
authors.initials: V
authors.lastname: Duong
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, http://chemistry.ucdavis.edu/faculty/department_faculty/mark_kurth.html.
authors.forename: Alex L
authors.initials: AL
authors.lastname: Bagdasarian
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, http://chemistry.ucdavis.edu/faculty/department_faculty/mark_kurth.html.
authors.forename: James C
authors.initials: JC
authors.lastname: Fettinger
authors.affiliation: Department of Chemistry, Department American University of Beirut, Institution, Beirut, Lebanon.
authors.forename: Makhlouf J
authors.initials: MJ
authors.lastname: Haddadin
authors.affiliation: Department of Chemistry, University of California, Davis, One Shields Avenue, Davis, California 95616, http://chemistry.ucdavis.edu/faculty/department_faculty/mark_kurth.html.
authors.forename: Mark J
authors.initials: MJ
authors.lastname: Kurth
keywords: Diversity Oriented Synthesis; Fused-ring systems; Heterocycle; Heterocyclization; Reduction