2,5-双去氢枞基-1,3,4-噻二唑和2,5-双去氢枞基-1,3,4-噁二唑的合成

Synthesis of 2,5-bisdehydroabietyl-1,3,4-thiadiazole and 2,5-bisdehydroabietyl-1,3,4-oxadiazole

以去氢枞酸为原料,经PCl3或SOCl2酰化得到去氢枞酰氯,与水合肼进行酰肼化反应得到N,N-二去氢枞酰基肼,再分别经过闭环和缩合反应得到目标化合物。研究了各化合物的反应条件;其中N,N-二去氢枞酰基肼的合成可在室温下完成,收率86.2%;合成2,5-双去氢枞基-1,3,4-噻二唑的最佳闭环剂是POCl3,在POCl3既做闭环剂又做溶剂的条件下,收率83.2%;2,5-双去氢枞基-1,3,4-噁二唑的合成中,在P2S5的作用下,以吡啶作为溶剂,收率可达到85.5%;整个合成路线中各步反应的收率都在80%以上,高收率得到目标化合物;其结构经IR、1HNMR和元素分析进行表征和确证。

2,5-Bisdehydroabietyl-1,3,4-thiadiazole and 2,5-bisdehydroabietyl-1,3,4-oxadiazole were synthesized using dehydroabietic acid as the raw material via the reaction with PCl3 or SOCl2,followed by hydration and cyclization.The synthesis conditions were studied in detail.N,N-bisdehydroabietyl hydrazine was obtained through hydration with dehydroabietic chloride at room temperature with 86.2% yield.2,5-Bisdehydroabietyl-1,3,4-thiadiazole was synthesized in POCl3,the optimum cyclization agent and solvent,with the product yield reaching 83.2%.2,5-Bisdehydroabietyl-1,3,4-oxadiazole was prepared via the reaction with P2S5,the optimum cyclization agent,and pyridine,the solvent,with the product yield reaching 85.5%.The structures of target products were characterized by IR,^1HNMR and elemental analysis.