title: Investigation of the one-pot synthesis of quinolin-2-(1H)-ones and the discovery of a variation of the three-component Ugi reaction.
abstract: Rapid access to the quinolin-2-(1H)-one scaffold is afforded by a sequential 4 component Ugi–Knoevenagel condensation of an aminophenylketone, an aromatic aldehyde possessing electron donating moieties, cyanoacetic acid and an aliphatic isocyanide, in moderate to good yields (49–71%). Interestingly, when the reaction is performed using aromatic aldehydes bearing electron withdrawing moieties or isocyanides containing aromatic or ester units, a mixture of a quinolin-2-(1H)-one and an α-amino amide (Ugi three-component adduct) is afforded in varying ratios. Further when the reaction is performed utilizing a combination of an isocyanide-containing aromatic or carbonyl unit, and an aldehyde possessing an electron withdrawing functionality, the Ugi three-component adduct is exclusively afforded. In our hands this new variation of the Ugi 3CR proved to be efficient and robust affording analogues in good yields (51–70%).
authors.affiliation: Chemistry, School of Environmental & Life Sciences, The University of Newcastle, University Drive, Callaghan, NSW 2308, Australia.
authors.forename: Christopher P
authors.initials: CP
authors.lastname: Gordon
authors.forename: Kelly A
authors.initials: KA
authors.lastname: Young
authors.forename: Lacey
authors.initials: L
authors.lastname: Hizartzidis
authors.forename: Fiona M
authors.initials: FM
authors.lastname: Deane
authors.forename: Adam
authors.initials: A
authors.lastname: McCluskey
mesh_terms: D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis*
chemical_list: D011804:Quinolines