7-甲氧基-4'-取代黄酮类化合物的合成

以2-羟基-4-甲氧基苯乙酮和4种对位取代的苯甲酰氯为原料,经过酯化、重排、成环3步反应方便地合成了4种7-甲氧基-4'-取代黄酮类化合物,并对各步反应条件进行了优化,得到的优化条件为:酯化反应:常温反应0.5～4 h,n(2-羟基-4-甲氧基苯乙酮)∶n(对位取代苯甲酰氯)=1∶(1.0～1.3);重排反应:反应温度30～60℃,反应时间2～6 h;成环反应:反应温度80～100℃,反应时间2～5 h,催化剂CH3COOH/H2SO4两者体积比(15～20)∶1。目标产物总收率50%～75%,HPLC分析纯度达95%以上。化合物结构经1HNMR、IR和MS证实。

Synthesis of 7-methoxy -4'-substituted flavones

In this paper,an expedient procedure to synthesize 7-methoxy-4′-substituted flavones from 2-hydroxy-4-methoxyacetophenone and 4-substitutedbenzoyl chlorides was discovered and optimized.The four flavones were obtained via the successive reactions of esterification,rearrangement and cyclization.The esterification was carried out for 0.5～4 h at room temperature,with the mole ratio of 1∶(1.0～1.3)(n(2-hydroxy-4-methoxyacetophenone)∶n(4-substitutedbenzoyl chlorides));the rearrangement was performed for 2~6 h at 30 ~ 60 ℃;the cyclization took place for 2~5 h at 80～100 ℃,with the catalyst of acetic acid/sulfuric acid(V(acetic acid)∶V(sulfuric acid)=(15～20)∶1).Under the optimum reaction conditions,the target products were obtained with overall yields of 50% ~ 75% and with a purity of more than 95%.The structures of the compounds were confirmed by 1HNMR,IR and MS.