Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 9, Issue 5, Pages 1419-1428Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob00029a
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- Australian Research Council
- John Morris Scientific (Australia)
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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 a-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%).
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