26952-92-1Relevant articles and documents
Nucleophilic substitution of hydrogen–the Boger reaction sequence as an approach towards 8-(pyridin-2-yl)coumarins
Fatykhov, Ramil F.,Savchuk, Maria I.,Starnovskaya, Ekaterina S.,Bobkina, Maria V.,Kopchuk, Dmitry S.,Nosova, Emiliya V.,Zyryanov, Grigory V.,Khalymbadzha, Igor A.,Chupakhin, Oleg N.,Charushin, Valery N.,Kartsev, Viktor G.
, p. 299 - 300 (2019)
5,7-Dimethoxy-8-(3,6-diphenylpyridin-2-yl)coumarins were obtained from 5,7-dimethoxycoumarins and 3,6-diphenyl-1,2,4-triazines via the protocol comprising aromatic SNH substitution in the triazine ring followed by the Boger transform
Formation of coumarins by palladium(II)-catalyzed reaction of phenols with ethyl acrylates
Aoki, Shinya,Oyamada, Juzo,Kitamura, Tsugio
, p. 468 - 472 (2005)
The reaction of phenols with ethyl acrylates in the presence of a Pd(OAc)2 catalyst in trifluoroacetic acid did not yield dihydrocoumarins but gave coumarins, in contrast to the reaction of phenols with propiolates. The addition of K2S2O8 as an oxidant increased the yield of coumarins. The reaction of several phenols with ethyl cinnamate, ethyl crotonate, or ethyl acrylate gave the corresponding coumarin derivatives in moderate to good yields. The coumarin formation competed with the oxidative coupling of electron-rich phenols, which reduced the product yield.
Synthesis and NMR of 4-Aryl-3,4-dihydrocoumarins and 4-arylcoumarins
Sun, Jie,Wang, Yanfeng
, p. 7753 - 7758 (2015/02/02)
This paper described the synthesis and 1H and 13C NMR chemical shifts of a series of 4-aryl-3,4-dihydrocoumarin and 4-arylcoumarin derivatives based on a combination of 1H and 13C NMR, HSQC and HMBC experiments.
Antioxidant and antitumor activities of 4-arylcoumarins and 4-aryl-3,4-dihydrocoumarins
Zhang, Keyun,Ding, Weixian,Sun, Jie,Zhang, Bin,Lu, Fujiao,Lai, Ren,Zou, Yong,Yedid, Gabriel
supporting information, p. 203 - 210 (2015/02/19)
Five 4-arylcoumarins (1c-g) and twelve 3,4-dihydro-4-arylcoumarins (2a-l) were synthesized and tested for antioxidant activity, antitumor activity, toxicity and structure-activity relationships analysis. 4-Arylcoumarins and 3,4-dihydro-4-arylcoumarins tha
Pd-catalyzed chemo-selective mono-arylations and bis-arylations of functionalized 4-chlorocoumarins with triarylbismuths as threefold arylating reagents
Rao, Maddali L.N.,Kumar, Abhijeet
, p. 6995 - 7005 (2015/03/14)
Cross-coupling reactions of differently substituted 4-chlorocoumarins were studied under palladium catalysis using triarylbismuths as threefold arylating reagents. The high reactivity of 4-chlorocoumarins was demonstrated delivering mono- and bis-arylation products in a chemo-selective manner. The reaction conditions employed are simple, robust and the threefold coupling reactivity of triarylbismuth reagents was witnessed with good to high yields in 2-4 h conditions. The utility of the methodology was explored in the synthesis of a few natural occurring neoflavones (3.27-3.30). In addition, the 4-arylcoumarin 3.1 product is a useful precursor for the preparation of (R)-tolterodine.
A convenient solid-phase synthesis of coumarins by TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes
Tang,Li, Wen,Gao, Zhangyong
experimental part, p. 907 - 912 (2012/05/20)
TMSOTf-catalyzed intramolecular seleno-arylation of tethered alkenes was performed using polystyrene-supported succinimidyl selenide as the selenium source. This catalytic process provides an efficient method for the regioselective synthesis of dihydrocou
Efficient synthesis and biological evaluation of 4-arylcoumarin derivatives
Sun, Jie,Ding, Wei Xian,Zhang, Ke Yun,Zou, Yong
, p. 667 - 670 (2012/01/13)
Two bioactive natural 4-arylcoumarins, 5,7,4′-trimethoxy-4- phenylcoumarin (1a), 5,7-dimethoxy-4-phenylcoumarin (1b) and five closely related derivatives 1c-g were synthesized. In vitro evaluation with a catechol subunit for antioxidant and antimicrobial activity, these compounds using standard methods showed that compounds 1d, 1f displayed promise radical scavenging activity and 1f was found to be the most active one against Bacillus dysenteriae.
Improved synthesis of coumarins by iron(III)-catalyzed cascade reaction of propiolic acids and phenols
Kutubi, Md. Shahajahan,Hashimoto, Takuya,Kitamura, Tsugio
experimental part, p. 1283 - 1289 (2011/05/19)
The reaction of propiolic acids with phenols in the presence of FeClAgOTf catalyst proceeded efficiently in a mixed solvent of trifluoroacetic acid and 1,2-dichloroethane, and provided coumarins in good to high yields. This iron-catalyzed reaction offers a much-improved synthesis of coumarins. Thieme Stuttgart New York.
Synthesis of coumarins and neoflavones through zinc chloride catalyzed hydroarylation of acetylenic esters with phenols
Leao, Raquel A. C.,Def.demoraes, Paula,Pedro, Marcella C. B. C.,Costa, Paulo R. R.
experimental part, p. 3692 - 3696 (2011/12/16)
Acetylenic esters react with oxygenated phenols under solvent-free conditions in the presence of only 5 mol% of zinc chloride as a catalyst to give coumarins and neoflavones in reasonable-to-good yields. Georg Thieme Verlag Stuttgart. New York.
Synthesis of coumarins by Pt-catalyzed hydroarylation of propiolic acids with phenols
Oyamada, Juzo,Kitamura, Tsugio
, p. 6918 - 6925 (2007/10/03)
Synthesis of coumarins from phenols and propiolic acids was examined by using a Pt catalyst such as PtCl2/AgOTf, K2PtCl4/AgOTf, and K2PtCl4/AgOAc. Propiolic acid reacted even with less reactive phenols in trifluoroacetic acid to give coumarins and dihydrocoumarins. In the case of substituted propiolic acids, phenylpropiolic acid and 2-octynoic acid, the reactions proceeded selectively to afford coumarins in good to high yields.
