仲胺介入的丙炔酸甲酯与亚胺的环合反应
收稿日期: 2015-12-31
修回日期: 2016-01-20
网络出版日期: 2016-02-24
Secondary Amine-Mediated Cyclization of Methyl Propiolate with Imines
Received date: 2015-12-31
Revised date: 2016-01-20
Online published: 2016-02-24
马鸿飞 , 黄浩 , 宿江岭 , 钮长盛 , 吴正光 , 卜洪忠 , 李玉峰 . 仲胺介入的丙炔酸甲酯与亚胺的环合反应[J]. 有机化学, 2016 , 36(6) : 1335 -1340 . DOI: 10.6023/cjoc201512050
A facile method for the synthesis of tetrahydropyrimidines is described. Diethylamine was treated with methyl propiolate to provide Michael adduct (β-amino acrylate). In the presence of organic acid, the cyclization of imines with β-aminoacrylateoccurred at room temperature and completed within several minutes to give tetrahydropyrimidines with liberation of ammonium salt. Formaldimines show good toleration to the reaction.
Key words： methylpropiolate; imine; amine-mediated reaction; tetrahydropyrimidines
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