应用芳基锂合成查尔酮

SYNTHESIS OF CHALCONES VIA LITHIUM ARYLIDES

苯基锂、2—甲氧基苯基锂和 2 ,4—二甲氧苯基锂分别与肉桂酸反应以 75 % ,6 5 % ,5 0 %的收率生成相应的查尔酮 ;2 ,6—二甲氧基苯基锂与肉桂酸不发生反应 ,但能与肉桂酸甲酯反应生成 2′,6′—二甲氧基查尔酮 ;类似的还制得了 2′,4′,6′—三甲氧基查尔酮和 2′,4′,4,6′—四甲氧基查尔酮。 2 ,4—二甲氧基苯基锂和 2 ,4,6—三甲氧基苯基锂也能与 γ—丁酸内酯反应分别生成 γ—羟丙基— (2 ,4—二甲氧基苯基 )酮和 γ—羟丙基— (2 ,4,6—三甲氧基苯基 )酮。

The phenyl Lithium, 2—methoxy phenyl Lithium and 2,4—dimethoxy phenyl Lithium reacted with the cinnamic acid to produce a corresponding chalcone in 75%, 56%, 50% yield, respectively. 2,6—Dimethoxyphenyl Lithium could not react with cinnamic acid, but reacted with methyl cinnamate to produce 2′,6′—dimethoxychalcone. Similarly, 2′,4′,6′,—trimethoxychalcone and 2′,4′,4,6′—tetramethoxychalcone were produced in the same manner. 2,4—Dimethyoxyphenyl Lithium and 2,4,6—trimethoxyphenyl Lithium could also react whth γ—butyrolactone to produce —hydroxypropyl (2,4—dimethoxyphenyl) ketone, and γ—hydroxy propyl (2,4,6—trmethoxyphenyl) ketone respectively. It is not found that the tertiary alcohol formed in the cases.