Molten urea serves both as a solvent and a reagent for the one-pot addition/cyclizations/fragmentation cascade which converts peri-alkynyl-9,10-anthraquinones into 2-R-7H-dibenzo[de,h]quinolin-7-ones – substituted analogues of Aporphinoid alkaloids.

Reaction of 1,2-diaminioethane (ethylenediamine) with electron-deficient alkynes leads to full scission of the C=C bond even in the absence of a keto group directly attached to the alkyne. This process involves oxidation of one of the alkyne carbons into C2 of a 2-R-4,5-dihydroimidazole with the concomitant reduction of the other carbon to a methyl group. The sequence of Sonogashira coupling with the ethylenediamine-mediated fragmentation described in this work can be used for selective formal substitution of halogen in aryl halides by a methyl group or a 4,5-dihydroimidazol-2-yl moiety.

Ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic effects. Understanding the molecular mechanisms of drug interaction with cell membranes is important to improving drug delivery, uptake by cells, possible side effects, etc. Double electron-electron resonance spectroscopy (DEER, also known as PELDOR) provides information on the nanoscale spatial arrangement of spin-labeled molecules. Here, DEER was applied to study (mono-)spin-labeled ibuprofen (ibuprofen-SL) in a bilayer of palmitoyl-oleoyl-sn-glycerophosphocholine (POPC). The results obtained show that the ibuprofen-SL molecules are located within a plane in each bilayer leaflet. At their low molar concentration in the bilayer χ, the found surface concentration of ibuprofen-SL is two times higher than χ, which can be explained by alternative assembling in the two leaflets of the bilayer. When χ > 2 mol%, these assemblies merge. The findings shed new light on the nanoscale spatial arrangement of ibuprofen in biological membranes.