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The five-member oxacyclic system of furan-2(5H)-ones, commonly named as γ-butenolides or properly as ∆α,β butenolides, is of high interest since many studies have proven its bioactivity. During past years, ∆α,β-butenolides have been important synthetic targets, with several reports of new procedures for their construction. A short compendium of these main different synthetic methodologies focused on the ∆α,β-butenolide ring formation, along with selected examples of compounds with relevant biological activities of these promising pharmaceutical entities is presented.
Biscarbonylmethylenetriphenylphosphoranes are versatile compounds derived from stabilized
α-carbonylmethylenetriphenylphosphoranes, mainly prepared by transylidation or by analogue
methodologies; other procedures include electrochemical oxidation, palladium-catalized insertions and
displacements reactions with tellurol esters, as well as the use of Bestmann’s ylide with different reagents
and reaction conditions. These biscarbonylmethylenetriphenylphosphoranes are usually converted
into acetylenes by thermal treatments. Biscarbonylmethylenetriphenylphosphoranes and their
oxidation products -vicinal tricarbonyl compounds- are of high importance due to their use as synthons
of more complex molecules and their promising biological activity.
A N-(2,4-diaryltetrahydroquinolin-1-yl) furan-2-carboxamide derivative, [4-(3,4-dimethoxyphenyl)-3,6-dimethyl-2-phenyl-3,4-dihydroquinolin-1(2H)-yl)](furan-2-yl)methanone, was synthesized in a two-step procedure from p-toluidine, benzaldehyde, and trans-methyl-isoeugenol as commercial starting reagents through a sequence of Povarov cycloaddition reaction/N-furoylation processes. The structure of the compound was fully characterized by IR, 1H, 13C-NMR, and X-ray diffraction data. Such types of derivatives are known as relevant therapeutic agents exhibiting potent anticancer, antibacterial, antifungal, anti-inflammatory, and immunological modulator properties.
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