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

doi:10.11944/j.issn.1000-0518.2015.05.140301

Chinese Journal of Applied Chemistry ›› 2015, Vol. 32 ›› Issue (5): 547-551.DOI: 10.11944/j.issn.1000-0518.2015.05.140301

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

CHEN Xiaojuan, ZHANG Wenjun, CHEN Jianxin^*

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

Received:2014-09-01 Revised:2014-10-20 Accepted:2014-12-17 Published:2015-05-05 Online:2015-05-05
Contact: CHEN Jianxin
Supported by:
Supported by the Shanxi Province Foundation for Returness(No.0713);the Natural Science Foundation of Shanxi Province(No.2012011046-9);the Foundation of Shanxi Normal University(No.SD2014CXXM-53)

Abstract

Abstract:

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, N-dimethylcarbamoyl(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.

Key words: carbamoylsilane, &alpha, -ketoamides, &alpha, -hydroxy-&alpha, -carbamoylamide, addition reaction

CLC Number:

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.

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

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