Laboratory of Organic Chemistry, Department of Chemistry, National and Kapodestrian University of Athens , Panepistimiopolis 15771, Athens, Greece.
J Org Chem. 2016 Aug 19;81(16):7023-8. doi: 10.1021/acs.joc.6b00488. Epub 2016 Jun 3.
A mild, one-pot, and environmentally friendly synthesis of amides from aldehydes and amines is described. Initially, a photoorganocatalytic reaction of aldehydes with di-isopropyl azodicarboxylate leads to an intermediate carbonyl imide, which can react with a variety of amines to afford the desired amides. The initial visible light-mediated activation of a variety of monosubstituted or disubstituted aldehydes is usually fast, occurring in a few hours. Following the photocatalytic reaction, addition of the primary amine at room temperature or the secondary amine at elevated temperatures leads to the corresponding amide from moderate to excellent yields without epimerization. This methodology was applied in the synthesis of Moclobemide, a drug against depression and social anxiety.
本文描述了一种从醛和胺合成酰胺的温和、一锅、环保的方法。首先，醛与二异丙基偶氮二甲酸酯的光有机催化反应导致中间羰基亚胺形成，它可以与各种胺反应得到所需的酰胺。最初可见光介导的各种单取代或二取代醛的快速活化通常在数小时内发生。光催化反应后，室温下加入伯胺或升高温度下加入仲胺，可得到相应的酰胺，产率中等至优秀，且无差向异构化。该方法应用于抗抑郁和社交焦虑药物莫达非尼的合成。
