71253-52-6Relevant academic research and scientific papers
Use of Nitrile Oxides in Synthesis. A Novel Synthesis of Chalcones, Flavanones, Flavones and Isoflavones
Thomsen, Ib,Torssell, Kurt B. G.
, p. 303 - 308 (2007/10/02)
Novel methodology is developed for a three-step synthesis of chalcones, flavanones, flavones and isoflavones. 1.Salicylaldoxime is chlorinated to the corresponding hydroxamoyl chloride in the presence of pyridine, and cycloadded to styrene and phenylacetylene. 2.The isoxazole derivatives formed are reductively cleaved over Raney-Ni to β-hydroxyketones or 1,3 diketones. 3.Acid-catalyzed cyclization gives the flavonoids.Use of ω-methoxy- or ω-dialkylamino-substituted styrenes (enamines) leads regioselectively to 4-aryl-substituted isoxazoles and derived isoflavones.
