61153-76-2Relevant articles and documents
Synthesis of Flavones via Application of the Nitrile Oxide and the Stille Reactions
Gothelf, Kurt V.,Torssell, Kurt B. G.
, p. 61 - 67 (2007/10/02)
Hydroxylated and methoxylated benzaldehyde oximes have been chlorinated, dehydrohalogenated and cycloadded to tributylstannylacetylene to give 3-aryl-5-tributylstannylisoxazoles in good to excellent yields.The palladium-catalyzed coupling reaction, the so-called Stille reaction, of hindered and electron-rich 2-iodophenols and a 2-iodo-1,4-benzoquinone with 3-aryl-5-tributylstannyl-isoxazoles gave 3-aryl-5-(2-hydroxyaryl)isoxazoles in moderate to excellent yields.The coupling reaction was studied under various conditions and with various Pd(II) and Pd(0) complexes.Reduction of the 3,5-diarylisoxazoles with H2/Raney-Ni, hydrolysis and acid-catalyzed cyclisation gave flavones.The synthesis of 2-iodo-3,5-dimethoxy-1,4-benzoquinone is described.