A new method for the synthesis of 2-hydroxy-3-nitro-1,4-naphthoquinones: application to regiospecific preparation of unsymmetrical nitrobiquinones.
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.
Yu
Min
M
Department of Biological, Chemical and Physical Sciences, Illinois Institute of Technology, Chicago, Illinois 60616, USA.
Malinakova
Helena C
HC
Stagliano
Kenneth W
KW
D006900:Hydroxylation; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism
D009285:Naphthoquinones; D009584:Nitrogen; C035342:1,4-naphthoquinone