Synthesis of furan and dihydrofuran derivatives via Feist–Benary reaction in the presence of ammonium acetate in aqueous ethanol

Tetrahydroindoles as Multipurpose Screening Compounds and Novel Sirtuin Inhibitors

“…In the next step, this intermediate was dehydrated under acidic conditions to yield 12 characterized by an aromatic furan structure. Water elimination using toluene in a Dean–Stark apparatus was not applicable due to the small amount of the intermediate 11 . Attempts to eliminate water in toluene without a distilling trap failed; only the carboxylic acid derivative 14 could be isolated.…”

“…The two nucleophilic centers reacted with the partial positive charged halide and carbonyl carbon atom likewise in order to form the bicyclic ring system 11.I nt he next step, this intermediate was dehydrated under acidic conditions to yield 12 characterized by an aromaticf uran structure. Water elimination using toluenei naDean-Stark apparatus [15] was not applicable due to the small amount of the intermediate 11.A ttempts to eliminate water in toluene without a distillingt rap failed;o nly the carboxylic acid derivative 14 could be isolated. To overcome this problem,wereplaced toluene with methanol, making use of the alcohol's ability to retain water by exothermic solvation.…”

“…Indole substructures are also implied in potent sirtuin inhibitors found in a rational screening approach of known adenosine mimetics . This screening afforded oxindoles (e.g., 3 ) and bisindolylmaleimides (e.g., 4 ), both scaffolds revealing low to sub‐micromolar inhibitory and SIRT2‐selective activity. From these findings we derived the hypothesis that less flat indole derivatives could be the searched‐for surrogate for compound class 1 .…”

“…[12,13] Indole substructures are also implied in potent sirtuin inhibitors found in ar ational screening approach of known adenosine mimetics. [14] This screening afforded oxindoles [15] (e.g., 3) and bisindolylmaleimides (e.g., 4), both scaffolds revealing low to sub-micromolar inhibitory and SIRT2-selective activity.F rom these findings we derived the hypothesis that less flat indole derivatives could be the searched-for surrogate for compound class 1.Ad atabase search for the former in ChEMBL 24 revealed fewer than 1000 compounds. Consequently,w es tarted as caffold-hopping approach from lipophilic splitomicin analogues that were difficult to optimize, to an ew tetrahydroindole scaffold.…”

Green synthesis of new thiouracilodepsipeptides in ionic liquid: One‐pot four‐component reaction of isocyanides

“…Other vital properties of RTILs including their density, viscosity, melting point, polarity, refractive index can be tuned by modifying the structures of their cation and anion components. As part of our current studies on the (IMCRs), [17][18][19][20][21] herein we report a one-pot four-component reaction to produce some thiouracilodepsipeptide derivatives (Scheme 1). [13] From this perspective, combining synthetic potentialities of MCRs with the dual properties of RTILs as solvents and promoters results in the emergence of promising strategies for the growth of costly ecocompatible organic synthesis procedures.…”