Yuan Chu-Ping, Xie Zhen-Zhen, Zheng Yu, He Jun-Tao, Guan Jian-Ping, Chen Hong-Bin, Xiang Hao-Yue, Chen Kai, Yang Hua
College of Chemistry and Chemical Engineering, Central South University, Changsha 410083, P. R. China.
Jiangxi Time Chemical Company, Ltd., Fuzhou 344800, P. R. China.
Chem Commun (Camb). 2023 Aug 17;59(67):10125-10128. doi: 10.1039/d3cc02744a.
Reported herein is the design and development of a new photo-induced amidation protocol with the readily available -chlorosulfonyl carbamate as an effective amidyl-radical precursor, which could be readily prepared from commercial low-cost chlorosulfonyl isocyanate (CSI) and alcohol feedstocks. The synthetic potency of this developed protocol was well demonstrated by direct amidation of various quinoxalin-2(1)-ones. The protocol could be further streamlined by implementing a one-pot/two-step/three-component process of CSI, alcohol, and quinoxalin-2(1)-one, with significantly improved reaction efficiency. This methodology offers an intriguing opportunity for rapid expansion of nitrogen-containing molecular complexity, thus inspiring comprehensive exploration of a new reaction mode of CSI reagent.
本文报道了一种新的光诱导酰胺化方法的设计与开发，该方法以易于获得的氯磺酰基氨基甲酸酯作为有效的酰胺基自由基前体，其可由市售低成本的氯磺酰异氰酸酯（CSI）和醇原料轻松制备。通过各种喹喔啉-2(1)-酮的直接酰胺化，充分证明了该开发方法的合成效力。通过实施CSI、醇和喹喔啉-2(1)-酮的一锅/两步/三组分过程，该方法可以进一步简化，反应效率显著提高。这种方法为含氮分子复杂性的快速扩展提供了一个有趣的机会，从而激发了对CSI试剂新反应模式的全面探索。
