Citation: Ma Hongfei, Huang Hao, Su Jiangling, Niu Changsheng, Wu Zhengguang, Bu Hongzhong, Li Yufeng. Secondary Amine-Mediated Cyclization of Methyl Propiolate with Imines[J]. Chinese Journal of Organic Chemistry, ;2016, 36(6): 1335-1340. doi: 10.6023/cjoc201512050 shu

Secondary Amine-Mediated Cyclization of Methyl Propiolate with Imines

a.
College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816
b.
Shandong Wanbo Chemical Industry Corporation, Zibo 255000
c.
Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093

Corresponding author: Li Yufeng, yufengli@njtech.edu.cn
Received Date: 31 December 2015
Revised Date: 20 January 2016

Figures(3)

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.
- methylpropiolate,
- imine,
- amine-mediated reaction,
- tetrahydropyrimidines
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1.
沈阳化工大学材料科学与工程学院沈阳 110142