123355-59-9Relevant academic research and scientific papers
Enantioselective N -Alkylation of Nitroindoles under Phase-Transfer Catalysis
Erkman, Kristin,J?rving, Ivar,K?ster, Kristjan,Kanger, T?nis,Leito, Ivo,Mart?nova, Jevgenija,Metsala, Andrus,Saame, Jaan,Trubits?n, Dmitri
, p. 1047 - 1059 (2020)
An asymmetric phase-transfer-catalyzed N -alkylation of substituted indoles with various Michael acceptors was studied. Acidities of nitroindoles were determined in acetonitrile by UV-Vis spectrophotometric titration. There was essentially no correlation between acidity and reactivity in the aza-Michael reaction. The position of the nitro group on the indole ring was essential to control the stereoselectivity of the reaction. Michael adducts were obtained in high yields and moderate enantioselectivities in the reaction between 4-nitroindole and various Michael acceptors in the presence of cinchona alkaloid based phase-transfer catalysts. In addition to outlining the scope and limitations of the method, the geometries of the transition states of the reaction were calculated.
Antimicrobial activity of quasi-enantiomeric cinchona alkaloid derivatives and prediction model developed by machine learning
Ga?parovic, Ana Cipak,Hrenar, Tomica,Mikelic, Ana,Milkovic, Lidija,Od?ak, Renata,Primo?ic, Ines,Ramic, Alma,Skocibu?ic, Mirjana,Sovic, Karlo
, (2021/06/16)
Bacterial infections that do not respond to current treatments are increasing, thus there is a need for the development of new antibiotics. Series of 20 N-substituted quaternary salts of cinchonidine (CD) and their quasi-enantiomer cinchonine (CN) were pr
Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: An effective route to dezocine
Li, Ruipeng,Liu, Zhenren,Chen, Liang,Pan, Jing,Zhou, Weicheng
supporting information, p. 1421 - 1427 (2018/06/29)
In order to prepare asymmetrically (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (3a), a key intermediate of dezocine, 17 cinchona alkaloid-derived catalysts were prepared and screened for the enantioselective alkylation of 1-methyl-7- methoxy-2-tetralone with 1, 5-dibromopentane, and the best catalyst (C7) was identified. In addition, optimizations of the alkylation were carried out so that the process became practical and effective.
Enantioselective phase-transfer-catalyzed intramolecular Aza-Michael reaction: Effective route to pyrazino-indole compounds
Bandini, Marco,Eichholzer, Astrid,Tragni, Michele,Umani-Ronchi, Achille
, p. 3238 - 3241 (2008/12/23)
(Chemical Equation Presented) Producing polycycles: A mild and direct stereocontrolled route to pharmacologically active pyrazino-indol-1-ones has been developed. The optimal phase-transfer conditions provide variously functionalized ring-closed compounds
