17947-70-5Relevant academic research and scientific papers
Synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarinviaa TsOH-mediated tandem reaction
Li, Chenyu,Liang, Yong,Ma, Zhishuang,Wang, Ding,Wang, Nana,Wang, Tao,Zhang, Zunting
supporting information, p. 10369 - 10372 (2020/09/16)
A concise and efficient method for the synthesis of 7-hydroxy-6H-naphtho[2,3-c]coumarin using available 1-(2-hydroxyphenyl)-2-phenylethanone and Meldrum's acid has been developed. This transformation involved a tandem aldol reaction/lactonization/Friedel-Crafts reaction to form a lactone ring and a benzene ring. It showed high atom economy with water and acetone as the byproducts. Mechanism studies demonstrated two roles of Meldrum's acid: (i) as the reagent for the tandem reaction, and (ii) as the catalyst for the Friedel-Crafts reaction. Moreover, the hydroxyl group of 7-hydroxy-6H-naphtho[2,3-c]coumarin was further functionalized efficiently by arylethynyl, aryl, and cyano groups to furnish D-π-A compounds with excellent fluorescence emissions (ΦF= 0.14-0.78).
Palladium-catalyzed carbonylation of benzylic ammonium salts to amides and esters: Via C-N bond activation
Yu, Weijie,Yang, Shuwu,Xiong, Fei,Fan, Tianxiang,Feng, Yan,Huang, Yuanyuan,Fu, Junkai,Wang, Tao
supporting information, p. 3099 - 3103 (2018/05/22)
An efficient palladium-catalyzed carbonylation reaction of readily available quaternary ammonium salts with CO is reported for the first time to afford arylacetamides and arylacetic acid esters via benzylic C-N bond cleavage. This protocol features mild reaction conditions under atmospheric pressure of CO, a redox-neutral process without an additional oxidant, and a broad substrate scope for various kinds of amines, alcohols and phenols.
A convenient one-pot completely stereoselective synthesis of trans-4-Hydroxystilbenes and its derivatives and X-ray structure of its precursor
Chhor, Rakeshwar B.,Singh, Kunwar A.,Nosse,Tandon, Vishnu K.
, p. 2519 - 2530 (2007/10/03)
The synthesis of E-isomer of 4-Hydroxystilbene and its derivatives 3 by reductive elimination of the carbonyl function in 2-phenyl-1-(4-hydroxyphenyl)ethan-1-one and its derivatives 2 and the X-ray structure of 2a are described.
Degenerate Transesterification of 3,5-Dimethylphenolate/3,5-Dimethylphenyl Esters in Weakly Polar, Aprotic Solvents. Reactions of Aggregates and Complex-Induced Proximity Effects
Jackman,Petrei,Smith
, p. 3451 - 3458 (2007/10/02)
The rates of exchange of the 3,5-dimethylphenolate ion between lithium 3,5-dimethylphenolate-d6 and a series of 3,5-dimethylphenyl esters have been determined in the weakly polar, aprotic solvents dioxolane, dimethoxyethane (DME), tetrahydrofuran (THF), and pyridine. The esters include the propionate, butyrate, methoxyacctate, β-methoxypropionate, 4-methoxybutyrate, 2-tetrahydrofuroate, 2-furoate, (N,N-dimethylamino)acetate, (methylthio)acetate, 2- and 4-pyridine-carboxylates, 2-pyridylacetate, 4-pyridylacetate, phenylacetate, andp-methoxy-,p-chloro-, and p-(trifluoromethyl)phenylacetates. The rates and kinetic orders of the reactions of 3,5-dimethylphenyl propionate in various solvents at 35°C gave the following second-order rate constants (104k2, L mol-1 sec-1) for the following major aggregate species: THF tetramer, 6.5; DME tetramer, 3.3 (40°C); dioxolane, 13, hexamer, 71; pyridine tetramer, 2.2, dimer, 29. For 3,5-dimethylphenyl β-methoxypropionate, the order of reactivity is dioxolane > DME > THF. These results are interpreted in terms of a preequilibrium in which a solvent on lithium in the tetramer is replaced by the ester. The rates of transesterification have been compared with the rates of hydrolysis in 30% aqueous ethanol for the above series of esters. Those esters that have a second Lewis base center proximal to the ester function show significantly increased reactivity in transesterification, which is attributed to a complex-induced proximity effect.
