新型噻吩并吡啶双杂环化合物的合成研究

Research on the Synthesis of a New Thieno[2,3-b]pyridine Bicycle Compound

以市场易得的苯乙酮、噻吩-2-甲醛为原料,经过羟醛缩合,得到的α,β-不饱和酮化合物2与2-氰基乙硫乙酰胺发生迈克尔加成反应环合生成2H-吡啶硫酮3;最后在碱性条件下,与溴代苯乙酮一步合成新型噻吩并吡啶双杂环化合物1,总收率为25.4%。该方法具有原料易得,操作简便,产物收率高等优点,可推广合成至该类其它取代的吡啶双杂环衍生物。

Starting from acetophenone and thiophene-2-formaldehyde, α, β-Unsaturated ketone compound 2 was synthesizes through Aldol condensation, the compound 2 reacted with 2-cyanoethylthioacetamide through Michael Cyclo-addition to afford 2 H-pyridine-thione 3, which reacted with bromo-acetophenone under basic conditions to form the target product 1 containing the novel thieno [2,3-b]pyridine bicycle structure through a two-step reaction in One-pot, total yield reaches about 75%. The preparation method has advantages of easy availability of raw materials, simple operation and high yield of the product,and can be applied the other pyridine bicycle derivatives.