652968-63-3Relevant academic research and scientific papers
Synthesis of Benzoaryl-5-yl(2-hydroxyphenyl)methanones via Photoinduced Rearrangement of (E)-3-Arylvinyl-4H-chromen-4-ones
Fan, Jinming,Wang, Tao,Li, Chenchen,Wang, Rui,Lei, Xiaoyu,Liang, Yong,Zhang, Zunting
supporting information, p. 5984 - 5987 (2017/11/10)
A concise and efficient photoinduced rearrangement of (E)-3-arylvinyl-4H-chromen-4-ones for the synthesis of benzoaryl-5-yl(2-hydroxyphenyl)methanones is described. Benzoaryl-5-yl-(2-hydroxyphenyl)methanones were obtained in 77-95% yields via the irradiation of (E)-3-arylvinyl-chromones in the 95% EtOH with a high-pressure mercury lamp at room temperature under Ar atmosphere. The reported method provides a novel procedure for the synthesis of α,α′-diaryl ketone derivatives without addition of any transition metals and oxidants or other additives. A plausible mechanism was proposed, and the rearrangement product was characterized by NMR, HRMS, and X-ray.
Syntheses of (E)- and (Z)-3-styrylchromones
Silva, Vera L. M.,Silva, Artur M. S.,Pinto, Diana C. G. A.,Cavaleiro, Jose A. S.,Vasas, Attila,Patonay, Tamas
experimental part, p. 1307 - 1315 (2009/12/05)
Several (E)- and (Z)-3-styrylchromones were prepared by two different methodologies, the Wittig reaction of chromone-3-carboxaldehyde with benzylic ylides and the Knoevenagel condensation of chromone-3-carboxaldehyde with phenylacetic acids in the presence of potassium tert-butoxide under microwave irradiation. The Knoevenagel reaction followed by a decarboxylation offered an efficient and diastereoselective method for preparing (E)-3-styrylchromones in a shorter reaction time. It was also demonstrated that phenylacetic acid can also be substituted with success by phenylmalonic acid. The stereochemistry of all products was assigned by NMR experiments.
Microwave-induced synthesis and regio- and stereoselective epoxidation of 3-styrylchromones
Patonay, Tamas,Kiss-Szikszai, Attila,Silva, Vera M. L.,Silva, Artur M. S.,Pinto, Diana C. G. A.,Cavaleiro, Jose A. S.,Jeko, Jozsef
body text, p. 1937 - 1946 (2009/04/04)
The microwave-assisted solvent-free synthesis of (E)-3-styrylchromones from 3-formylchromones and phenylmalonic acid on sodium acetate support has been developed; the method affords the styryl derivatives in moderate to good yields and with complete diastereoselectivity. Protocols for the highly regioselective epoxidation of (E)- and (Z)-3-styrylchromones have been elaborated. Treatment of the alkenes with dimethyldioxirane led to the exclusive formation of 3-(3-aryloxiran-2-yl)chromones with complete diastereoselectivity, whereas treatment with hydrogen peroxide under alkaline conditions afforded the corresponding 2,3-epoxy-3-styrylchromanones as the only products. Epoxidation performed in the presence of chiral, nonracemic cinchona-alkaloid-based quaternary ammonium salts allowed the synthesis of enantiomerically enriched 2,3-epoxy-3-styrylchromanones, but with only moderate ee values. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Wittig reactions of chromone-3-carboxaldehydes with benzylidenetriphenyl phosphoranes: A new synthesis of 3-styrylchromones
Sandulache, Angela,Silva, Artur M. S.,Pinto, Diana C. G. A.,Almeida, Lucia M. P. M.,Cavaleiro, Jose A. S.
, p. 1592 - 1598 (2007/10/03)
An efficient route to 3-styrylchromones has been developed and applied to syntheses of several new derivatives. Wittig reactions of chromone-3- carboxaldehydes with some benzylic ylides gave a diastereomeric mixture of (E) and (Z)-3-styrylchromones that a
