1217-93-2Relevant academic research and scientific papers
Arylation of ortho-Hydroxyarylenaminones by Sulfonium Salts and Arenesulfonyl Chlorides: An Access to Isoflavones
Mkrtchyan, Satenik,Iaroshenko, Viktor O.
, p. 4896 - 4916 (2021/04/12)
Herein we disclose three new methods for the straightforward and efficient synthesis of 3-arylchromones following the arylation of ortho-hydroxyarylenaminones by vast diversities of bench-stable and easy-to-use sulfonium salts and arenesulfonyl chlorides.
C-H Functionalization via Remote Hydride Elimination: Palladium Catalyzed Dehydrogenation of ortho-Acyl Phenols to Flavonoids
Zhao, Xiaomei,Zhou, Jiabin,Lin, Shuying,Jin, Xukang,Liu, Renhua
supporting information, p. 976 - 979 (2017/03/14)
Although deprotonation of electron-poor C-H bonds to carbon anions with bases has long been known and widely used in organic synthesis, the hydride elimination from electron-rich C-H bonds to carbon cations or partial carbocations for the introduction of nucleophiles is a comparatively less explored area. Here we report that the carbonyl β-C(sp3)-H bond hydrogens of ortho-acyl phenols could be substituted by intramolecular phenolic hydroxyls to form O-heterocycles, followed by dehydrogenation of the O-heterocycle into flavonoids. The cascade reaction is catalyzed by Pd/C without added oxidants and sacrificing hydrogen acceptors.
Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging
Miao, Jianzhuang,Cui, Huaqing,Jin, Jing,Lai, Fangfang,Wen, Hui,Zhang, Xiang,Ruda, Gian Filippo,Chen, Xiaoguang,Yin, Dali
, p. 881 - 884 (2015/02/19)
Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is
Pd-Catalyzed efficient cross-couplings of 3-iodochromones with triarylbismuths as substoichiometric multicoupling organometallic nucleophiles
Rao, Maddali L. N.,Venkatesh, Varadhachari,Jadhav, Deepak N.
experimental part, p. 2597 - 2600 (2010/01/16)
An efficient cross-coupling of 3-iodochromones with triarylbismuths under catalytic palladium conditions is reported. Triarylbismuths were employed as substoichiometric multicoupling nucleophiles for the synthesis of a variety of substituted isoflavones.
Ligand Coupling Route to Isoflavanones and Isoflavones
Santhosh, K. C.,Balasubramanian, K. K.
, p. 224 - 225 (2007/10/02)
Phenylation of 3-phenylsulfonylchroman-4-ones using Ph3BiCO3 leading to the synthesis of isoflavanones and isoflavones is reported.
Oxidation of Flavanones using Thallium(III) Salts: A New Route for the Synthesis of Flavones and Isoflavones
Khanna, Mahavir S.,Singh, Om V.,Garg, Chandra P.,Kapoor, Ram P.
, p. 2565 - 2568 (2007/10/02)
When treated with thallium(III) acetate in acetic acid or acetonitrile, flavanones undergo facile dehydrogenation to afford flavones whereas, upon treatment with thallium(III) toluene-p-sulfonate or thallium(III) nitrate in propionitrile or acetonitrile, respectively, they undergo oxidative 2,3-aryl migration to give isoflavones in high yield.
Oxidative 1,2-aryl rearrangement in flavanones using thallium(III) p-tolylsulphonate (TTS): A new useful route to isoflavones
Singh,Garg,Kapoor
, p. 2747 - 2750 (2007/10/02)
Oxidation of flavanones using thallium(III) p-tolylsulphonate (prepared in situ by the reaction of thallium(III) acetate and p-toluene sulphonic acid) in propionitrile leads to 1,2-aryl shift providing a new useful route to the synthesis of isoflavones.
