title: Metal-free arylation of ethyl acetoacetate with hypervalent diaryliodonium salts: an immediate access to diverse 3-aryl-4(1H)-quinolones.
abstract: A clean arylation protocol of ethyl acetoacetate was developed using hypervalent diaryliodonium salts under mild and metal-free conditions. The scope of the reaction, using symmetric and unsymmetric iodonium salts with varying sterics and electronics, was examined. Further, this method has been applied for the synthesis of antimalarial compound ELQ-300, which is currently in preclinical development.
authors.affiliation: Department of Chemistry, University of South Florida, 4202 E Fowler Ave., Tampa, FL 33620, United States.
authors.forename: Andrii
authors.initials: A
authors.lastname: Monastyrskyi
authors.affiliation: Department of Chemistry, University of South Florida, 4202 E Fowler Ave., Tampa, FL 33620, United States.
authors.forename: Niranjan K
authors.initials: NK
authors.lastname: Namelikonda
authors.affiliation: Department of Chemistry, University of South Florida, 4202 E Fowler Ave., Tampa, FL 33620, United States.
authors.forename: Roman
authors.initials: R
authors.lastname: Manetsch
mesh_terms: D000090:Acetoacetates / Q000737:chemistry*; D000962:Antimalarials / Q000138:chemical synthesis* / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D008670:Metals / Q000737:chemistry*; D015394:Molecular Structure; D009861:Onium Compounds / Q000737:chemistry*; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D015363:Quinolones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: C000601913:6-Chloro-7-methoxy-2-methyl-3-(4-(4-(trifluoromethoxy)phenoxy)phenyl)quinolin-4(1H)-one; D000090:Acetoacetates; D000962:Antimalarials; D008670:Metals; D009861:Onium Compounds; D011804:Quinolines; D015363:Quinolones; D007455:Iodine; C024840:ethyl acetoacetate