硫代丁内酯拼接吡唑啉酮双螺环化合物的合成

Synthesis of Novel Bispiro[pyrazolone-thiobutyrolactone]Derivatives

以3-异硫氰酸酯取代的硫代丁内酯1为合成子,在有机催化剂DABCO作用下,与各种取代的吡唑啉酮烯烃2发生Michael加成与环化反应,获得了9个未见文献报道的新型硫代丁内酯拼接吡唑啉酮双螺环化合物3a~3i,产率70%~77%,dr 2/1~9/1,其结构经^(1)H NMR,^(13)C NMR和HR-MS(ESI-TOF)表征,通过单晶进一步确定了化合物3c的构型。该类化合物含有螺环丁内酯和螺环吡唑啉酮生物活性骨架,对医药行业具有重要的潜在价值。

In this paper,3isothiocyanato thiobutyrolactone 1 and various alkylidene pyrazolones 2 were used as raw materials,the Michael/cyclization reaction occurred.Nine novel bispiro[pyrazolone-thiobutyrolactone]derivatives 3a~3i were obtained.The yields and dr of 3a~3i were 70%~77%and 2/1~9/1,respectively.The structures of products 3 were characterized by ^(1)H NMR,^(13)C NMR and HR-MS(ESI-TOF).The configuration of compound 3c was further determined by single crystals.These compounds contain two potential bioactive skeletons of spiropyrazolone and spirothiobutyrolactone,which has important potential value for the pharmaceutical industry.