title: Aryl-free radical-mediated oxidative arylation of naphthoquinones using o-iodoxybenzoic acid and phenylhydrazines and its application toward the synthesis of benzocarbazoledione.
abstract: Oxidative arylation of naphthoquinones has been developed through combination of o-iodoxybenzoic acid with arylhydrazines under mild conditions at open atmosphere. Arylated naphthoquinones with different electronic properties were obtained in moderate to good yields. The postulated radical mediated mechanism is supported by radical trapping experiments. Developed protocol for direct arylation of naphthoquinones has been extended toward short, high yielding, and an effective synthesis of antitumor-antibiotic precursor such as benzocarbazoledione.
authors: Department of Pharmaceutical Sciences and Technology, Institute of Chemical Technology , Matunga, Mumbai 400019, India.
authors: Pravin
authors: P
authors: Patil
authors: Abhay
authors: A
authors: Nimonkar
authors: Krishnacharya G
authors: KG
authors: Akamanchi
mesh_terms: D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002384:Catalysis; D005609:Free Radicals / Q000737:chemistry*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D007462:Iodobenzenes / Q000737:chemistry*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D010659:Phenylhydrazines / Q000737:chemistry*
chemical_list: C000592529:5H-benzo(b)carbazole-6,11-dione; D002227:Carbazoles; D005609:Free Radicals; D006576:Heterocyclic Compounds, 4 or More Rings; D007462:Iodobenzenes; D009285:Naphthoquinones; D010659:Phenylhydrazines; C476101:o-iodoxybenzoic acid; D010165:Palladium