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Citation: CHEN Xiaojuan, ZHANG Wenjun, CHEN Jianxin. Novel Synthesis of α-Hydroxy-α-carbamoyl Amide Compounds[J]. Chinese Journal of Applied Chemistry, ;2015, 32(5): 547-551. doi: 10.11944/j.issn.1000-0518.2015.05.140301 shu

Novel Synthesis of α-Hydroxy-α-carbamoyl Amide Compounds

1.
College of Chemistry and Material Science, Shanxi Normal University, Linfen, Shanxi 041004, China

Corresponding author: CHEN Jianxin,
Received Date: 1 September 2014
Available Online: 17 December 2014
Fund Project: 山西省留学回国人员基金(0713) (0713)山西省自然科学基金(2012011046-9) (2012011046-9)山西师范大学基金(SD2014CXXM-53)资助项目 (SD2014CXXM-53)

α-Hydroxy-α-carbamoylamides are important synthetic intermediates and also serve as valuable agents in medicinal chemistry.Herein,a novel method for synthesis of α-hydroxy-α-carbamoylamides was developed and the reaction mechanism involving two intermediates was proposed.Good yields of α-hydroxy-α-carbamoylamides or α-trimethylsiloxy-α-carbamoylamides are obtained by the addition of N,Ndimethylcarbamoyl(trimethyl) silane to a series of α-ketoamides under anhydrous condition at 105℃.Their structures were characterized by elemental analysis,¹H NMR,¹³C NMR and IR spectra.The steric hindrance is found to be an important factor in the addition reaction and the electronic effect can influence the rate of the reaction.
- carbamoylsilane,
- α-ketoamides,
- α-hydroxy-α-carbamoylamide,
- addition reaction
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