Zinc- and indium-promoted conjugate addition-cyclization reactions of ethenetricarboxylates with propargylamines and alcohol: Novel methylenepyrrolidine and methylenetetrahydrofuran syntheses
Zinc- and indium-promoted conjugate addition-cyclization reactions of ethenetricarboxylates with propargylamines and alcohol: Novel methylenepyrrolidine and methylenetetrahydrofuran syntheses
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DOI：
10.1021/jo0602118
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发表时间：
2006-04-28
影响因子：
3.6
通讯作者：
Kakiuchi, K
中科院分区：
文献类型：
--
作者：
Morikawa, S;Yamazaki, S;Kakiuchi, K
开发了一种新的锌和铟促进的共轭加成环化反应，以提供含氮和氧的五元杂环。在 ZnBr2 或 InBr3 存在下，乙烯三羧酸酯与炔丙胺（1 当量）反应，以高产率提供亚甲基吡咯烷。在室温下化学计量使用ZnBr2或InBr3以及在80℃下使用InBr(3)(-)Et3N催化是有效的。乙烯三羧酸酯与炔丙醇在 ZnBr2 或 InBr3 存在下反应，得到亚甲基四氢呋喃。
A new zinc- and indium-promoted conjugate addition-cyclization reaction to afford nitrogen- and oxygen-containing five-membered heterocycles has been developed. Reaction of ethenetricarboxylates with propargylamines (1 equiv) in the presence of ZnBr2 or InBr3 afforded methylenepyrrolidines in high yields. The stoichiometric use of ZnBr2 or InBr3 at room temperature and the catalytic use of lnBr(3)(-) Et3N at 80 degrees C were effective. Reaction of ethenetricarboxylates with propargyl alcohol in the presence of ZnBr2, or InBr3 afforded methylenetetrahydrofurans.