Aza-Michael reactions in ionic liquids. A facile synthesis of β-amino compounds

Electron-deficient olefins undergo smoothly aza-Michael reactions with a wide range of amines in ionic liquids in the absence of any acid catalyst to produce the corresponding β-amino compounds in excellent yields with high 1,4-selectivity. The recovered ionic liquids can be reused in subsequent reactions without loss of activity. Owing to the high polarity of ionic liquids, the enones show enhanced reactivity thereby reducing reaction times and improving the yields significantly

Three-component coupling reactions in ionic liquids: an improved protocol for the synthesis of 1,4-dihydropyridines

Three-component condensation of aldehyde, β-ketoester and methyl 3-aminocrotonate proceeds smoothly in 1-n-butyl-3-methylimidazolium tetrafluoroborate [bmim]BF<SUB>4</SUB> or 1-n-butyl-3-methylimidazolium hexafluorophosphate [bmim]PF<SUB>6</SUB> ionic liquids at room temperature under mild conditions to afford the corresponding 1,4-dihydropyridine derivatives in high yields. The recovered activated ionic liquids are recycled for four to five runs with no loss in activity

Enantioselective synthesis of hyperparathyroidism agent Cinacalcet hydrochloride

A simple and efficient route has been developed for enantioselective synthesis of hyperparathyroidism agent (R)-Cinacalcet. The synthesis started from commercially available triflouromethyl benzaldehyde and 1-(naphthalen-1-yl) ethanone and completed in 8 steps with an overall yield 18.5%. The key reactions involved are Corey-Bakshi-Shibata chiral reduction and reductive amination

Baeyer-Villiger oxidations in ionic liquids. A facile conversion of ketones to esters and lactones

A variety of cyclic and acyclic ketones underwent readily oxidation with m-chloroperbenzoic acid (m-CPBA) in ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate [bmim]BF<SUB>4</SUB> to afford esters/lactones with high selectivity, ease of product separation and in excellent chemical yields. The reaction proceeded smoothly in ionic liquid without the need of any additional acid or base catalyst. The ketones show enhanced reactivity in ionic liquids thereby reducing reaction times and improving the yields significantly

Iodine as a mild, efficient, and cost-effective reagent for the synthesis of cis-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acids

Arylimines generated in situ from aromatic aldehydes and anilines undergo smooth coupling with homophthalic anhydride in the presence of 10 mol% of molecular iodine under mild and neutral conditions to afford the corresponding cis-1-oxo-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acids in excellent yields with high cis selectivity. The use of iodine makes this procedure simple, convenient, and cost-effective

Enantioselective synthesis of hyperparathyroidism agent Cinacalcet hydrochloride

503-507A simple and efficient route has been developed for enantioselective synthesis of hyperparathyroidism agent (R)-Cinacalcet. The synthesis started from commercially available triflouromethyl benzaldehyde and 1-(naphthalen-1-yl) ethanone and completed in 8 steps with an overall yield 18.5%. The key reactions involved are Corey-Bakshi-Shibata chiral reduction and reductive amination