α -羟基-α -氨甲酰基酰胺类化合物的合成新方法

doi:10.11944/j.issn.1000-0518.2015.05.140301

摘要/Abstract

摘要：

N, N-二甲氨酰基三甲基硅烷与一系列α -羰基酰胺在无水无氧、105 ℃的条件下反应, 较高产率地合成了α -羟基-α -氨甲酰基酰胺类化合物或α -三甲基硅氧基-α -氨甲酰基酰胺衍生物。其结构用元素分析、¹H NMR、¹³C NMR和IR等技术手段进行了表征。通过研究反应机理和影响反应的因素发现, 在α -羰基上连的烃基的空间位阻是该加成反应的重要影响因素, 而电子效应则影响反应的速率。提出了可能的反应机理。

关键词: 氨甲酰基硅烷, &alpha, -羰基酰胺, &alpha, -羟基-&alpha, -氨甲酰基酰胺, 加成反应

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

中图分类号:

陈晓娟, 张文俊, 陈建新. α -羟基-α -氨甲酰基酰胺类化合物的合成新方法[J]. 应用化学, 2015, 32(5): 547-551.

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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