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高等学校化学研究 ›› 2015, Vol. 31 ›› Issue (2): 212-217.doi: 10.1007/s40242-015-4388-8

• Articles • 上一篇    下一篇

An Efficient and Green Approach to Synthesizing Enamines by Intermolecular Hydroamination of Activated Alkynes

ZENG Ruijie, SHENG Hongting, RAO Bo, FENG Yan, WANG Hao, SUN Yehua, CHEN Man, ZHU Manzhou   

  1. School of Chemistry and Chemical Engineering, Anhui University, Hefei 230601, P. R. China
  • 收稿日期:2014-10-15 修回日期:2014-12-10 出版日期:2015-04-01 发布日期:2014-12-29
  • 通讯作者: SHENG Hongting, FENG Yan E-mail:sht_anda@126.com;fy70@163.com
  • 基金资助:

    Supported by the National Natural Science Foundation of China(Nos.20902001, 21102001), the Natural Science Foundation of the Educational Department of Anhui Province, China(No.KJ2014A013), the "211" Project of Anhui University(China) and the Doctor Research Start-up Fund of Anhui University(China).

An Efficient and Green Approach to Synthesizing Enamines by Intermolecular Hydroamination of Activated Alkynes

ZENG Ruijie, SHENG Hongting, RAO Bo, FENG Yan, WANG Hao, SUN Yehua, CHEN Man, ZHU Manzhou   

  1. School of Chemistry and Chemical Engineering, Anhui University, Hefei 230601, P. R. China
  • Received:2014-10-15 Revised:2014-12-10 Online:2015-04-01 Published:2014-12-29
  • Contact: SHENG Hongting, FENG Yan E-mail:sht_anda@126.com;fy70@163.com
  • Supported by:

    Supported by the National Natural Science Foundation of China(Nos.20902001, 21102001), the Natural Science Foundation of the Educational Department of Anhui Province, China(No.KJ2014A013), the "211" Project of Anhui University(China) and the Doctor Research Start-up Fund of Anhui University(China).

摘要:

An efficient, atom-economic and green approach to synthesizing enamines was developed by intermolecular hydroamination of activated alkynes with high yields under catalyst- and solvent-free conditions. β-Dimethylamino-acrylate derivatives were also obtained with high yields. In the synthetic process of the derivatives, N,N-dimethylformamide(DMF) pretreated with metal Na, was used as reactant instead of dimethylamine gas. The proposed synthetic method can be used for the synthesis of (E)-ethyl-3-(dimethylamino)acrylate(3cl), and provide a new possible way to the synthesis of Quinolones.

关键词: Enamine, Hydroamination, Activated alkyne, Catalyst-free, Solvent-free, N,N-Dimethylformamide

Abstract:

An efficient, atom-economic and green approach to synthesizing enamines was developed by intermolecular hydroamination of activated alkynes with high yields under catalyst- and solvent-free conditions. β-Dimethylamino-acrylate derivatives were also obtained with high yields. In the synthetic process of the derivatives, N,N-dimethylformamide(DMF) pretreated with metal Na, was used as reactant instead of dimethylamine gas. The proposed synthetic method can be used for the synthesis of (E)-ethyl-3-(dimethylamino)acrylate(3cl), and provide a new possible way to the synthesis of Quinolones.

Key words: Enamine, Hydroamination, Activated alkyne, Catalyst-free, Solvent-free, N,N-Dimethylformamide