N-(Hetero)aryl-2-imidazolines: an emerging privileged motif for contemporary drug design

15N labeling and analysis of13C–15N and1H–15N couplings in studies of the structures and chemical transformations of nitrogen heterocycles

“…The application of 15 In the case of the reaction between azirine derivative 146* and phthalimide, the tricyclic product 153* 57 was isolated. The structure of 153* was identied by measurements of 13 C-15 N SSCCs ( 1 J C9b-N2 ¼ 7 Hz and 1 J C3-N2 ¼ 8 Hz), which were registered for sp 3 -hybridized carbon atoms (Scheme 41). Additionally, the 1 J HN -couplings were not detected in the 1D 1 H and 15 N NMR spectra.…”

“…Nitrogen heterocycles are a ubiquitous class of organic compounds that include azirine, azetidine, azole, azine and azepine derivatives and their fused analogs. These structures are inherent in drug design [1][2][3][4][5][6][7] and natural compounds, 8,9 in catalysis for cross-coupling and asymmetric synthesis reactions, 10,11 in materials science as metal complexes with luminescent properties, [12][13][14] in ligands for the separation of lanthanides 15 and in high-density energy materials. 16,17 At rst glance, it seems that establishing the structure of poly-nitrogen-containing compounds can be achieved by general NMR methods suitable for carbon-containing compounds; however, this statement is not correct.…”

Imidazoline synthesis: mechanistic investigations show that Fe catalysts promote a new multicomponent redox reaction

“…Imidazolines are a class of compounds of strong interest in pharmacy 1,2 and medicine 3,4 which is continuously enhanced by new developments, as for example for imaging 5,6 and antibacterial 7 purposes. Similarly, their established industrial significance 8,9 has been recently reinforced by new applications as ligands for enantioselective catalysis 10 as well as corrosion additives.…”

Electrophilically activated nitroalkanes in reaction with aliphatic diamines en route to imidazolines

“…Not surprisingly, imidazalines are oen regarded nowadays as one of the privileged scaffolds for drug discovery. 11,12 Normally, preparation of 2-imidazolines 4 is very straightforward and involves acylation of 1,2-diamines 2 with carbonyl compounds 1 (acyl, thioacyl, carbamoyl halides, esters, carboxylic acids, or nitriles) and subsequent cyclocondensation of the formed b-aminocarboxamide intermediate 3 (Scheme 1). [13][14][15][16] For number of years we were interested in electrophilic activation of nitroalkanes and their reactions with different nucleophilic species.…”