Tankam Theeranon, Srisa Jakkrit, Sukwattanasinitt Mongkol, Wacharasindhu Sumrit
Nanotec-CU Center of Excellence on Food and Agriculture, Department of Chemistry, Faculty of Science , Chulalongkorn University Bangkok 10330 , Thailand.
J Org Chem. 2018 Oct 5;83(19):11936-11943. doi: 10.1021/acs.joc.8b01824. Epub 2018 Sep 21.
In this work, we developed a catalyst-free amination of 2-mercaptobenzoxazoles on water under microwave irradiation. The product, 2-aminobenzoxazoles, was successfully produced via direct amination with various amines in moderate to high yields. The formal synthesis of Suvorexant, a medication for the treatment of insomnia, was accomplished using a developed amination process. The reaction was completed in an hour at 100-150 °C in a microwave reactor without the use of external catalyst or additive. Key benefits of this process include an on-water reaction, short reaction time, being scalable and catalyst-free, and use of 2-mercaptobenzoxazoles as an inexpensive starting material having low environmental impact in its preparation.
在本工作中，我们开发了一种在微波辐射下于水相中进行的无催化剂2-巯基苯并恶唑胺化反应。通过与各种胺直接胺化，以中等到高的产率成功制备了产物2-氨基苯并恶唑。使用所开发的胺化方法完成了用于治疗失眠的药物苏沃雷生的形式合成。该反应在微波反应器中于100 - 150°C下1小时内完成，无需使用外部催化剂或添加剂。该方法的主要优点包括水相反应、反应时间短、可扩展且无催化剂，以及使用2-巯基苯并恶唑作为廉价起始原料，其制备过程对环境影响小。
