56862-41-0Relevant academic research and scientific papers
BTK Inhibitors and uses thereof
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, (2020/05/02)
The invention discloses a bruton's tyrosine kinase (BTK) inhibitor and use thereof. Specifically, the invention provides heteroaromatic compounds or stereoisomers, geometrical isomers, tautomers, racemates, nitrogen oxides, hydrates, solvates, metabolites and pharmaceutically acceptable salts or prodrugs thereof, and pharmaceutical compositions containing the heteroaromatic compounds; the invention also discloses use of the heteroaromatic compounds or the pharmaceutical compositions containing the heteroaromatic compounds in preparation of medicines; the medicines can be used for treating autoimmune diseases, inflammatory diseases or proliferative diseases.
Synthesis of Imidazolidin-2-ones and Imidazol-2-ones via Base-Catalyzed Intramolecular Hydroamidation of Propargylic Ureas under Ambient Conditions
Casnati, Alessandra,Perrone, Antonio,Mazzeo, Paolo P.,Bacchi, Alessia,Mancuso, Raffaella,Gabriele, Bartolo,Maggi, Raimondo,Maestri, Giovanni,Motti, Elena,Stirling, András,Ca, Nicola Della
, p. 3477 - 3490 (2019/03/11)
The first organo-catalyzed synthesis of imidazolidin-2-ones and imidazol-2-ones via intramolecular hydroamidation of propargylic ureas is reported. The phosphazene base BEMP turned out to be the most active organo-catalyst compared with guanidine and amidine bases. Excellent chemo- and regioselectivities to five-membered cyclic ureas have been achieved under ambient conditions, with a wide substrate scope and exceptionally short reaction times (down to 1 min). A base-mediated isomerization step to an allenamide intermediate is the most feasible reaction pathway to give imidazol-2-ones, as suggested by DFT studies.
Construction of the Oxazolidinone Framework from Propargylamine and CO2 in Air at Ambient Temperature: Catalytic Effect of a Gold Complex Featuring an L2/Z-Type Ligand
Inagaki, Fuyuhiko,Maeda, Kakeru,Nakazawa, Kenta,Mukai, Chisato
, p. 2972 - 2976 (2018/06/27)
The metal-catalyzed carboxylation of propargylamines with aerial CO2 at room temperature to form 5-methyleneoxazolidin-2-one derivatives has been developed. In this reaction, the catalyst [Au(dpbF)]X featuring a Z-type ligand gave the best results, presumably due to the σ-acceptance of the borane atom.
Robust Silver(I) Catalyst for the Carboxylative Cyclization of Propargylic Alcohols with Carbon Dioxide under Ambient Conditions
Song, Qing-Wen,He, Liang-Nian
, p. 1251 - 1258 (2016/04/26)
Inspired by the bulkier bis(triphenylphosphine)-silver cation-induced mechanism of propargylic alcohols and carbon dioxide through the alkyl carbonate intermediate, a robust dual-component catalytic system consisting of silver acetate and tetraheptylammonium bromide was rationally developed for the synthesis of α-methylene cyclic carbonates under ambient conditions without employing any additional organic base and ligand. This is one of the most effective catalysts reported to date for this conversion, with a very high turnover number of up to 6024, probably due to the synergistic effect of Lewis basic and Lewis acidic species for the activation of both propargylic alcohol and carbon dioxide by the formation of the alkyl carbonate with a bulkier counterion. Notably, this catalyst also worked well for the carboxylative cyclization of propargylic amines with carbon dioxide with the highest turnover number of 544.
Silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for stereoselective preparation of (E)-iodovinyloxazolidinones
Sekine, Kohei,Kobayashi, Ryo,Yamada, Tohru
, p. 1407 - 1409 (2015/11/24)
The silver-catalyzed three-component reaction of propargylic amines, carbon dioxide, and N-iodosuccinimide for the stereoselective synthesis of (E)-iodovinyloxazolidinones was developed. The silver-catalytic system could be applied to various propargylic amines to afford the corresponding iodovinyloxazolidinones in high yields. The structure of the oxazolidinone was confirmed by X-ray structure analysis to be the Eisomer for the geometry of the exo-olefin. The silver-catalyzed cyclization and replacement of silver with the iodine group in the intermediate were thought to be crucial steps.
An unprecedented Pd-catalyzed, water-promoted sequential oxidative aminocarbonylation-cyclocarbonylation process leading to 2-oxazolidinones
Gabriele, Bartolo,Plastina, Pierluigi,Salerno, Giuseppe,Mancuso, Raffaella,Costa, Mirco
, p. 3319 - 3322 (2008/02/12)
An unprecedented, Pdl2-catalyzed, sequential oxidative aminocarbonylation-cyclocarbonylation process, leading to 2-oxazolidinone derivatives 3 in good to excellent yields starting from readily available α,α-disubstituted 2-ynylamines 1 and secondary amines 2, is reported. In the case of an α-monosubstituted substrate, the initially formed 2-oxazolidinone derivative underwent shift of the double bond to give a 3H-oxazol-2-one derivative in excellent isolated yield.
Superbase catalysis of oxazolidin-2-one ring formation from carbon dioxide and prop-2-yn-1-amines under homogeneous or heterogenous conditions
Costa, Mirco,Chiusoli, Gian Paolo,Taffurelli, Davide,Dalmonego, Giulio
, p. 1541 - 1546 (2007/10/03)
N-alkyl-substituted prop-2-yn-1-amines and N-tri-, tetra- and penta-alkyl-substituted guanidines or other strong organic bases assemble under the action of carbon dioxide to afford carbamates, from which methyleneoxazolidinones 2 are formed by ring closure. If alkyl or cycloalkyl chains of appropriate length are present in the guanidines the reaction readily occurs under heterogenous conditions without solvent.
Copper(I)-Catalyzed Amination of Propargyl Esters. Selective Synthesis of Propargylamines, 1-Alken-3-ylamines, and (Z)-Allylamines
Imada, Yasushi,Yuasa, Mari,Nakamura, Ishin,Murahashi, Shun-Ichi
, p. 2282 - 2284 (2007/10/02)
Copper(I)-catalyzed aminations of propargyl phosphates and acetates proceed under mild reaction conditions to give the corresponding propargylamines which are precursors of 1-alken-3-ylamines and (Z)-allylamines.
