摘要
本文首次报道了异黑豆素类似物,6-非环糖基-4′,7-二羟基黄酮的合成。以2,4-二羟基苯甲酸为原料,溴化和脱羧后以苄基作为羟基保护基,通过Grignard反应获得具有各种不同侧链的中间体7,7氢解脱除苄基再用Fries重排或Friedel-Crafts反应得到了C-乙酰化产物,接着用碱缩合生成查尔酮,经I_2/H_2SO_4/DMSO氧化环合得到目标产物1、2、3。
A series of analogs of isobayin wore synthesized using 2, 4-dihydroxybenzoic acid as a starting material, through bromination, decarboxylation, benzylation and Grignard reaction to give the 4-substituted-1, 3-dibenzyloxy-bonzenes (7) in good yields. Then, 7 were debenzylated by catalytic hydrogenation, and C-acetylated via Fries rearrangement or Friedol-Crafts reaction (HOAc/ZnCl_2). These C-acetyl derivatives, 16, 17 and 18 were condensed with p-hydroxybenzaldehyde in the presence of KOH/EtOH/H_2O to give 30—60% yield of the corresponding chalcones 22,23 and 24, which gave the target flavones 1, 2 and 3 by oxidation with I_2/H_2SO_4/DMSO in 24——46% yields.
出处
《化学学报》
SCIE
CAS
CSCD
北大核心
1990年第12期1191-1198,共8页
Acta Chimica Sinica
