Synthesis of eight-membered hydroquinolines related to alkaloid skeletons via addition of 4-hydroxycoumarin or 4-hydroxypyran-2-one to quinolinium salts

Site‐Selective 1,4‐Difunctionalization of Nitrogen Heteroaromatics for Constructing Vinylidene Heterocycles

“…A plausible mechanistic pathway, which is based on recent literature reports [7,18] and control experiment (SI, Scheme S1), is shown in Scheme 2. First, quinoline reacts with benzyl bromide to form a N‐alkylazaarene zwitterionic species 4 A‐1 .…”

“…The reaction was performed with a 1:10 ratio of product 4 a (0.2 mmol): Et 3 SiH and 10 mol% B(C 6 F 5 ) 3 in the open air at 100 °C for 16 h. Effective reduction of the nitro group and C=C double bond were achieved (Table 6b). A plausible mechanistic pathway, which is based on recent literature reports [7,18] and control experiment (SI, Scheme S1), is shown in Scheme 2. First, quinoline reacts with benzyl bromide to form a N-alkylazaarene zwitterionic species 4 A-1.…”

Different routes for the construction of biologically active diversely functionalized bicyclo[3.3.1]nonanes: an exploration of new perspectives for anticancer chemotherapeutics

“…The strategy also worked well when the coumarin derivative was replaced by a 4-hydroxypyrone derivative ( 372 ), giving high yields of bicycle 373 (71–88%) (Scheme 85b). 169 This communication was immediately followed by another letter, where a series of novel benzoxazocine derivatives were achieved by applying the same C -alkylation and concomitant O -cyclization strategy. Active methylene containing 1,3-diketones ( 374 ) were utilized this time to get condensed with N -alkylquinoliniums ( 367 ), resulting in the formation of methylene-bridged benzoxazocines ( 375 ) (yield 61–83%) in an identical manner (Scheme 85c).…”

Comparison of the synergistic effect of counterions on the inhibition of mild steel corrosion in acid solution: electrochemical, gravimetric and thermodynamic studies

“…1. Compounds 1 and 2 were prepared according to the general procedures known from the literature, 27,28 except that ethanol was used as the solvent instead. Keeping the ratio of quinoline to benzyl bromide at 1 : 1.1 ought to have provided the best conditions for the synthesis of 1.…”