Yoon Jeong A, Lim Changjin, Han Young Taek
College of Pharmacy, Dankook University, Cheonan-si, South Korea.
School of Pharmacy, Jeonbuk National University, Jeonju-si, South Korea.
Front Chem. 2020 Sep 4;8:772. doi: 10.3389/fchem.2020.00772. eCollection 2020.
A preliminary study to develop a novel synthetic method for 3-aryl-5-azaisocoumarins was performed herein. The cycloisomerization of -pyranonyl propargylamines in the AgOTf-catalyzed system efficiently afforded the desired 3-aryl-5-azaisocoumarins in a highly regioselective manner. This unprecedented method is expected as an expedient alternative synthetic route to 5-azaisocoumarins because the regioselectivity problem is circumvented, and it is easier to introduce substituents on the pyridine ring compared to previously reported intramolecular lactonization approaches.
本文开展了一项初步研究，旨在开发一种合成3-芳基-5-氮杂异香豆素的新方法。在AgOTf催化体系中，-吡喃酮基炔丙胺的环异构化反应以高度区域选择性的方式高效地得到了所需的3-芳基-5-氮杂异香豆素。这种前所未有的方法有望成为合成5-氮杂异香豆素的便捷替代合成路线，因为它规避了区域选择性问题，并且与先前报道的分子内内酯化方法相比，在吡啶环上引入取代基更容易。
