375373-63-0Relevant academic research and scientific papers
Regioselective syntheses of 6-(1,1-dimethylallyl)- and 8-(3,3-dimethylallyl) chrysins
Daskiewicz, Jean-Baptiste,Bayet, Christine,Barron, Denis
, p. 3589 - 3595 (2007/10/03)
The first regioselective syntheses of 6-(1,1-dimethylallyl)- and 8-(3,3-dimethylallyl) chrysins have been designed. Claisen rearrangement of protected 5-O-(3,3-dimethylallyl) chrysin in N,N-diethylaniline at 200-217°C gave selective access to the 8-(3,3-dimethylallyl) isomer. Similar rearrangement in N,N-diethylbutylamine at 140-160°C, or in cycloheptane/Eu(fod)3 at 100°C, led to the formation of the 6-(1,1-dimethylallyl) isomer. Four different protecting groups for position 7 of chrysin have been compared, and found to follow the order of interest Bz>MOM>TBDPS>MEM.
Rearrangement of 5-O-prenyl flavones: A regioselective access to 6-C-(1,1-dimethylallyl)- and 8-C-(3,3-dimethylallyl)-flavones
Daskiewicz, Jean-Baptiste,Bayet, Christine,Barron, Denis
, p. 7241 - 7244 (2007/10/03)
Regioselective control of the Claisen rearrangement of 7-MEM-5-prenyl chrysin was achieved by microwave irradiation. The nature of the products was influenced by the irradiation power and the type of solvent. Irradiation at 750 W in N,N-diethylaniline specifically yielded the 8-(3,3-dimethylallyl) para-rearranged product while refluxing in N,N-diethylbutylamine gave selective access to the 6-(1,1-dimethylallyl) ortho-rearranged compound.
