71589-55-4Relevant academic research and scientific papers
Comparative studies of palladium and copper-catalysed γ-arylation of silyloxy furans with diaryliodonium salts
Alexander, Taylor S.,Clay, Travis J.,Maldonado, Bryan,Nguyen, Johny M.,Martin, David B.C.
, p. 2229 - 2238 (2019/03/06)
The γ-arylation of substituted silyl-activated butenolides has been studied using a broad scope of unsymmetrical hypervalent diaryliodonium salts via a palladium- or copper-catalysed coupling reaction, yielding interesting reactivity trends. The mild catalytic conditions and coupling partner variability provide access to synthetically useful building blocks toward the pursuit of aryl-lactone containing natural products and allows for facile diversification.
Lewis base-catalyzed electrophilic lactonization of selenyl bromide resin and facile solid-phase synthesis of furan-2(5H)-one derivatives
Jun He, Rong,Chun Zhu, Bing,Wang, Yu Guang
, p. 523 - 528 (2014/07/07)
A facile solid-phase synthesis approach was developed for the rapid synthesis of multi-substituted furan-2(5H)-one derivatives libraries. The synthetic strategy included the selenyl bromide resin-induced electrophilic lactonization catalyzed by Lewis base, lithiation, nucleophilic substitution and oxidation-elimination of the selenium resins. The advantages of the new method are good yields, high purity, straightforward operations and high diversity of the products, lack of odor, and good stability of the selenium resins. Copyright
Synthesis and cytotoxic activity of γ-aryl substituted α-alkylidene-γ-lactones and α-alkylidene-γ-lactams
Albrecht, Anna,Koszuk, Jacek F.,Modranka, Jakub,Rozalski, Marek,Krajewska, Urszula,Janecka, Anna,Studzian, Kazimierz,Janecki, Tomasz
, p. 4872 - 4882 (2008/12/23)
A series of 5-aryl-3-alkylidenedihydrofuran-2(3H)-ones 6a-g″ and 11a,b as well as 5-aryl-3-methylidenepyrrolidin-2-ones 10a-c and 12 were synthesized starting from 4-aryl-2-diethoxyphosphoryl-4-oxobutanoates 3a-g. Reaction sequence includes reduction or reductive amination of the carbonyl group, lactonization or lactamization step and finally the Horner-Wadsworth-Emmons olefination of aldehydes using thus obtained 5-aryl-3-diethoxyphosphoryl-3,4-dihydrofuran-2(5H)-ones 5a-g″ or 5-aryl-3-diethoxyphosphorylpyrrolidin-2-ones 9a-c. Furanones 6 and 11, as well as pyrrolidinones 10 and 12, were evaluated in vitro against mouse leukemia cell line L-1210 and two human leukemia cell lines HL-60 and NALM-6. Several of the obtained furanones proved to be very potent against all three cell lines with IC50 values lower than 6 μM. Structure-activity relationships of these compounds, as well as 5-alkyl or 5-arylmethyl-3-methylidenedihydrofuran-2(3H)-ones 13a-e, previously obtained in our laboratory, are discussed.
