叔胺催化的Sulfa-Michael-Aldol串联反应合成羟基取代的四氢噻吩类化合物  

Tertiary Amine Catalyzed Sulfa-Michael-Aldol Cascade Reaction for the Synthesis of Hydroxy-Substituted Tetrahydrothiophenes

作　　者：白亚茹 卢新宇 牛瑞 张琰图[1] 蔺军兵 BAI Ya-ru;LU Xin-yu;NIU Rui;ZHANG Yan-tu;LIN Jun-bing(College of Chemistry and Chemical Engineering, Yan’an University, Yan’an 716000, China)

机构地区：[1]延安大学化学与化工学院,陕西延安716000

出　　处：《合成化学》2022年第2期133-139,共7页Chinese Journal of Synthetic Chemistry

基　　金：延安大学研究生教育创新计划项目(YCX2020012);陕西省大学生创新创业训练计划项目(S202010719139)。

摘　　要：探究了叔胺1,4-二氮杂二环[2.2.2]辛烷(DABCO)催化的2,5-二羟基-1,4-二噻烷和羟基取代查尔酮的sulfa-Michael-aldol串联环化反应。考察了催化剂对反应收率的影响,以最高79%的收率合成了15个多取代的四氢噻吩化合物。其代表产物的结构经X-ray单晶衍射实验确证,化合物结构经^(1)H NMR,^(13)C NMR,IR和HR-MS(ESI)表征。Tertiary amine 1,4-diazabicyclo[2.2.2]octane(DABCO)catalyzed sulfa-Michael-aldol cascade reaction of 1,4-dithiane-2,5-diol and hydroxy-substituted chalcones has been developed.The effect of catalyst on reaction efficiency was evaluated,and fifteen novel trisubstituted tetrahydrothiophenes were readily synthesized in satisfactory yields(up to 79%yield).The structure of the representative example was confirmed by X-ray analysis,and the products obtained were characterized by ^(1)H NMR,^(13)C NMR,IR and HR-MS(ESI).

关 键 词：四氢噻吩 有机催化 叔胺 串联反应 合成 sulfa-Michael-aldol反应 

分 类 号：O626[理学—有机化学]