58113-16-9Relevant academic research and scientific papers
Organolead-mediated Arylation of Allyl β-Ketoesters: A Selective Synthesis of Isoflavanones and Isoflavones
Donnelly, Dervilla M.,Finet, Jean-Pierre,Rattigan, Bernard A.
, p. 1729 - 1736 (2007/10/02)
Arylation of A-ring substituted and unsabstituted 3-allyloxycarbonylchroman-4-ones with aryllead(IV) triacetates followed by selective catalytic deallyloxycarbonylation affords isoflavanones or isoflavones in high overall yields.The highest yield in the arylation step was observed in the reaction of 5,7-dimethoxychroman-4-one with the more hindered 2,4,6-trimethoxyphenyllead triacetate.
Aryllead mediated synthesis of isoflavanone and isoflavone derivatives
Donnelly, Dervilla M. X.,Fitzpatrick, Brendan M.,O'Reilly, Bernadette A.,Finet, Jean-Pierre
, p. 7967 - 7976 (2007/10/02)
The reaction of aryllead (IV) triacetates with 3-(phenylthio)-chroman-4-one and 2-p-methoxyphenyl-3-(phenylthio)-chroman-4-one derivatives was carried out in chloroform in presence of pyridine to afford moderate to quantitative yields of the corresponding hindered 3-aryl-3-phenylthiochroman-4-one derivatives. Removal of the phenylthio group by oxidation with dimethyldioxirane led to the corresponding isoflavones and 2-p-methoxyphenylisoflavones, and by reduction with a large excess of nickel boride to the isoflavanones and 2-(4′-anisyl)-isoflavanones respectively. In the 2-p-methoxyphenyl series the nickel boride reduction of the compounds bearing ortho-substituted 3-aryl groups gave the chalcones which were recyclised under basic catalysis.
