The substrate scope, the mechanistic aspects of the gold-catalyzed oxazole synthesis, and substrates with different aliphatic, aromatic, and functional groups in the side chain were investigated. Even molecules with several propargyl amide groups could easily be converted, delivering di- and trioxazoles with interesting optical properties. Furthermore, the scope of the gold(I)-catalyzed alkylidene synthesis was investigated. Further functionalizations of these isolable intermediates of the oxazole synthesis were developed and chelate ligands can be obtained. The use of Barluenga's reagent offers a new and mild access to the synthetically valuable iodoalkylideneoxazoles from propargylic amides, this reagent being superior to other sources of halogens.
Gold(I)-triflimide (AuNTf 2 )complexes of H-KITPHOS and o-MeO-KITPHOS have been prepared and shown to be efficient catalysts for a range of intramolecular cyclisations to afford phenols, acylindenes, alkylidene oxazoles, tetrahydropyrans and lactones, in the majority of cases these catalysts are superior to those previously reported.
Based on the gold-catalyzed synthesis of methyleneoxazolines, a one-pot combination with an Alder-ene reaction was developed. For azodicarboxylates, good to very good yields (51-99%) of the oxazolemethylhydrazinedicarboxylates were achieved with 3 mol% of the Gagosz catalyst, [Ph(3)PAuNTf(3)]. In a less-selective reaction, 4-phenyl-3H-1,2,4-triazol-3,5(4H)-dione gave lower yields (41-49%) of the corresponding oxazolemethylphenyltriazolidinediones. Overall, five new bonds were formed. Tetracyanoethylene afforded a cyclobutane derivative through a [2+2] cycloaddition reaction at -40 °C, but only 45% of the spiro compound was obtained. The less-readily available KITPHOS ligands on gold gave even higher yields at lower catalyst loadings (2 mol%), but longer reaction times were required.
Stadt und Vergnügen waren um 1900 eng miteinander verbunden. Tanzveranstaltungen und Theater, Kino und Kneipen boten den Großstadtbewohnern vielfältige Möglichkeiten, ihrem Bedürfnis nach Freizeitgestaltung und Unterhaltung nachzugehen. Gleichzeitig prägten die Vergnügungsangebote zunehmend das Stadtbild. Ausgehend von der Beobachtung, dass die Herausbildung einer modernen Vergnügungskultur nicht ohne die Urbanisierung gedacht werden kann und dass die Vergnügungskultur eine wichtige Rolle im Prozess der Anpassung an das Leben in der Großstadt spielte, untersucht der Band die Wechselwirkungen zwischen Metropole und Vergnügen um 1900. Das Spektrum der Beiträge reicht vom Vergnügungsviertel bis zum Kiezvergnügen, von Mode auf der Theaterbühne und politischen Massenveranstaltungen bis hin zu Alpenbällen und Musikautomaten.
The reaction of N‐propargylamides (I) and azodicarboxylates (II) provides functionalized oxazoles (III) in high yields through a five‐step cycloisomerization/Alder‐ene reaction pathway.
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