Aryllead Triacetates as Synthons for the Synthesis of Biflavonoids. Part 2. Synthesis of Garcinia-Type Biflavonoid
Arylation of 3-(phenylsulfonyl)chroman-4-one 1 with simple aryllead triacetates affords the corresponding 3-aryl-3-(phenylsulfonyl)chroman-4-one in 64-74percent yield.However, no reaction took place with the hindered 2,4,6-trimethoxyphenyllead triacetate
Donnelly, Dervilla M. X.,Fitzpatrick, Brendan M.,Ryan, Sarah M.,Finet, Jean-Pierre
p. 1797 - 1802
(2007/10/02)
Aryllead mediated synthesis of isoflavanone and isoflavone derivatives
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.
Donnelly, Dervilla M. X.,Fitzpatrick, Brendan M.,O'Reilly, Bernadette A.,Finet, Jean-Pierre
p. 7967 - 7976
(2007/10/02)
Ligand Coupling Route to Isoflavanones and Isoflavones
Phenylation of 3-phenylsulfonylchroman-4-ones using Ph3BiCO3 leading to the synthesis of isoflavanones and isoflavones is reported.
Santhosh, K. C.,Balasubramanian, K. K.
p. 224 - 225
(2007/10/02)
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