科研之友
微信
新浪微博
Facebook
分享链接
摘要
In order to promote further development of green chemistry, an easy and efficient new method for the synthesis of fuctionalized enamines from alpha,beta-vicinal bromoamine compounds promoted by combination of potassium carbonate and thiouea in water at room temperature was developed, and the nearly quantitative yields of much products were obtained(up to 99%). 23 structurally different substrates were investigated. The results indicate that the protocol could tolerate various vicinal bromoamine compounds including alpha,beta-vicinal bromoamine esters and ketones. During the elimination process of HBr from vicinal bromoamine compounds, the corresponding intermediate aziridines must be formed. Herein, no matter the substrate was alpha-amino-beta-bromo or alpha-bromo-beta-amino in structurally, the aziridines skeleton in structurally was similar to each other formed from the intramolecular nucleophilic replacement reaction fashion. Because of ring-open reaction of the aziridines have full regiospecificity, the obtained final products are full regiospecificity, too. The structures of all products were confirmed by H-1 NMR, C-13 NMR and HRMS analysis. When the gram level substrate was tested with this protocol, the nearly quantitative yield of the product was obtained, too. This result indicated that the new method could be possible applied in the industrialization.
- 出版日期2014-7-10
- 单位陕西师范大学
