Solvent-controlled two-step one-pot syntheses of α-X (X = Br or Cl) enamino ketones/esters and 3-(2,5-dioxopyrrolidin-1-yl)acrylate by using terminal carbonyl alkynes

Xiao Yun Chen; Shuxia Yuan; Yan Chen; Chenyang Sun; Yaonan Tang; Guang Chen; Baocheng Zhu; Kaiwei Chen; Shaojun Zheng; Xiaofang Cheng

doi:10.1039/D1OB01308D

Solvent-controlled two-step one-pot syntheses of α-X (X = Br or Cl) enamino ketones/esters and 3-(2,5-dioxopyrrolidin-1-yl)acrylate by using terminal carbonyl alkynes†

Xiao Yun Chen,

‡*^a Shuxia Yuan,^a Yan Chen,^a Chenyang Sun,^a Yaonan Tang,^a Guang Chen,^a Baocheng Zhu,^a Kaiwei Chen,^a Shaojun Zheng^a and Xiaofang Cheng^a

Author affiliations

* Corresponding authors

^a School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Mengxi Road No. 2, Zhenjiang, P. R. China
E-mail: chenxy@just.edu.cn

Abstract

A new two-step one-pot aminobromination/chlorination of carbonyl alkynes has been achieved via a Michael addition of aliphatic secondary amines and subsequent β-bromination/chlorination of the obtained enamines to afford various α-X (X = Br or Cl) enamino ketones/esters in moderate to good yields. A solvent-controllable protocol has been developed to produce versatile 3-(2,5-dioxopyrrolidin-1-yl)acrylates in moderate yields by using toluene as the solvent and chain alkyl propiolates as alkynyl substrates.

This article is part of the themed collection: Synthetic methodology in OBC

Organic & Biomolecular Chemistry

Solvent-controlled two-step one-pot syntheses of α-X (X = Br or Cl) enamino ketones/esters and 3-(2,5-dioxopyrrolidin-1-yl)acrylate by using terminal carbonyl alkynes†

Abstract

Supplementary files

Article information

Download Citation

Permissions

Solvent-controlled two-step one-pot syntheses of α-X (X = Br or Cl) enamino ketones/esters and 3-(2,5-dioxopyrrolidin-1-yl)acrylate by using terminal carbonyl alkynes

Social activity

Search articles by author

Spotlight

Advertisements