Access to trifluoromethylated 4-alkoxy-2-pyrones, pyridones and quinolones

A Novel Non-Peptidic Agonist of the Ghrelin Receptor with Orexigenic Activity In vivo

“…Compound 10 was prepared according to a known procedure and spectral characteristics were consistent with previously reported data31.…”

“…Methyl 2,2-difluoro-2-(fluorosulfonyl) acetate (MFSDA) was used as the reagent for the trifluoromethylation of pyridone 14 to give novel pyridone 8 3031. Before returning to in depth biological studies, the prepared pyridone 8 was deemed not toxic in the two cell lines tested: Hek293a-GHS-R1a and mHypoE-N38 using the resazurin toxicity assay (for details, see SI, Figure S1).…”

Facile Reagent‐Free Synthesis of Furo[3,2‐c]pyridinones and Their Polynuclear Analogues with DDQ as Precursor

“…All the N-substituted 4-hydroxypyridinones were simply synthesized through the aminolysis of readily available triacetic acid lactone with various amines including aliphatic, aromatic amines, and alkoxyamines with the modified methods in some cases. [5] In general, all the substrates examined are applicable for this oxidative annulation, giving rise to the corresponding furopyridinones with good efficacy, as is shown in Table 1. The aliphatic substituents afforded good yields, whether they are chained or branched, cyclic or not.…”

“…Thus, the reaction conditions were not optimized further, and directly applied to the substrate scope investigation under the optimized conditions as follows: DDQ (3 equiv) for compounds 1 in MeCN at room temperature. All the N ‐substituted 4‐hydroxypyridinones were simply synthesized through the aminolysis of readily available triacetic acid lactone with various amines including aliphatic, aromatic amines, and alkoxyamines with the modified methods in some cases . In general, all the substrates examined are applicable for this oxidative annulation, giving rise to the corresponding furopyridinones with good efficacy, as is shown in Table .…”

Combinatorial Chemistry Online Volume 17, Issue 7, July 2015

“…As the introduction of a trifluoromethyl group to a molecule can have dramatic and beneficial effects in terms of lipophilicity and bioavailability, a route to afford a library of novel trifluoromethylated 2-pyrones, 2-pyridones and a 2-quinolone has been reported. Reactions using methyl fluorosulfonyldifluoroacetate as the trifluoromethylating agent have generated products in moderate to good yield [6].…”