title: A new method for the synthesis of 2-hydroxy-3-nitro-1,4-naphthoquinones: application to regiospecific preparation of unsymmetrical nitrobiquinones.
abstract: Novel 2-hydroxy-3-nitro-1,4-naphthoquinones were synthesized by an improved method utilizing nitronium tetrafluoroborate in high yields. A subsequent conversion to 2-chloro-3-nitro-1,4-naphthoquinones and a substitution of the chlorine by hydroxyquinone anions yielded 3-nitro-2,2'-binaphthoquinones with a complete regiocontrol.
authors.affiliation: Department of Biological, Chemical and Physical Sciences, Illinois Institute of Technology, Chicago, Illinois 60616, USA.
authors.forename: Min
authors.initials: M
authors.lastname: Yu
authors.forename: Helena C
authors.initials: HC
authors.lastname: Malinakova
authors.forename: Kenneth W
authors.initials: KW
authors.lastname: Stagliano
mesh_terms: D006900:Hydroxylation; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D009285:Naphthoquinones; D009584:Nitrogen; C035342:1,4-naphthoquinone