Tetrahedron ( IF 2.1 ) Pub Date : 2018-05-26 , DOI: 10.1016/j.tet.2018.05.059 Lu Zhou , Fangchong Yuan , Yidi Zhou , Wenwen Duan , Min Zhang , Hongmei Deng , Liping Song
One-pot, four-component reactions of 1,2-diphenylpyrazolidine-3,5-dione, ethyl 4,4,4-trifluoroacetoacetate, aromatic aldehyde and ammonium acetate afforded highly functionalized ethyl 8-hydroxy-1,4-dioxo-2,3,6,10-tetraphenyl-8-(trifluoromethyl)-2,3,7-triazaspiro[4.5]decane-9-carboxylate derivatives 5 in good yields. The most advantage of this reaction was the high diastereoselectivity because only one diastereoisomer 5 was produced. The effect of NH4OAc and solvents on the reaction efficiency and yield was briefly investigated. Meanwhile, the further transformation of hemi-aminal moieties to the corresponding dehydrated product was also achieved under the mild reaction conditions. And a plausible reaction mechanism for the formation of products 5 was illustrated based on the control experiments.
中文翻译:
在无催化剂的条件下,对三氟甲基化螺哌啶方便的一锅式MCR
1,2-二苯基吡唑烷-3,5-二酮,4,4,4-三氟乙酰乙酸乙酯,芳族醛和乙酸铵的一锅四组分反应得到高度官能化的乙基8-羟基-1,4-二氧杂-2- ,3,6,10-四苯基-8-(三氟甲基)-2,3,7-三氮杂螺[4.5]癸烷-9-羧酸酯衍生物5的收率很高。该反应的最大优点是非对映异构体选择性高,因为仅产生一种非对映异构体5。简要研究了NH 4 OAc和溶剂对反应效率和收率的影响。同时,在温和的反应条件下,半氨基部分进一步转化为相应的脱水产物。以及形成产物的合理反应机理5 根据对照实验进行了说明。