Synthesis and reactivity of two new trichloromethyl substituted dihydroisoquinoline-derived oxaziridines

Hypolipidemic effect of dihydroisoquinoline oxaziridine in high-fat diet-fed rats

“…The oxaziridine 3 was previously reported in our earlier research work to be an agent for the transfer of oxygen on organosulfides [23]. The oxaziridine 3 used in the current study was synthesized starting from the commercial tertiary alcohol 1 (Scheme 1).…”

Synthesis and reactivity of new dihydroisoquinoline-derived oxaziridines

“…In our previous work, 33 the introduction of the two attractor groupings, trichloromethyl in position 1 and nitro group in position 7, onto the dihydroisoquinoline skeleton of the function was noted to being able to oxidize sulfide into sulfoxide with heating at reflux for 7 h. Herein, we show that with the introduction of a p-chlorophenyl group in position 1 and of two electron-withdrawing nitro groups in position 7 and in the phenyl group, it was possible to oxidize the sulfide to sulfoxide at room temperature.…”

“…In fact, the resulting oxaziridine 9 being able to oxidize sulfide into sulfoxide in the best time compared with the previously reported result in the literature. 31,33 Next, In order to check the oxidizing properties of oxaziridine 9, the results of oxygen transfer of other sulfides into the corresponding sulfoxides was studied using a set of structurally diverse sulfides, in the presence of acid, in dichloromethane, at room temperature.…”

“…The dihydroisoquinoline oxaziridines have previously been reported to be promising agents for the transfer of oxygen to organosulfides in the presence and absence of acid. [30][31][32][33] The substitution at position 1 onto the dihydroisoquinoline skeleton has a marked influence in the formation of sulfoxide or nitrone products from the oxidation reactions of the oxaziridines. 31,33 We have noted a significant variation in reaction times when we changed the structure of oxaziridine, most notably the substitution at position 1.…”

“…[30][31][32][33] The substitution at position 1 onto the dihydroisoquinoline skeleton has a marked influence in the formation of sulfoxide or nitrone products from the oxidation reactions of the oxaziridines. 31,33 We have noted a significant variation in reaction times when we changed the structure of oxaziridine, most notably the substitution at position 1. Indeed, the unsubstituted dihydroisoquinoline oxaziridine can oxidize quickly the p-tolylmethyl sulfide to the sulfoxide, 32 whereas oxygen transfer is slowest in the presence of steric hindrance, in position 1, of the oxaziridine.…”