Peptide Chemistry Research Institute, K. N. Toosi University of Technology, P.O. Box 15875-4416, 19697-64499 Tehran, Iran.
Organisch-Chemisches Institut der Universitaet Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany.
Org Lett. 2021 May 7;23(9):3524-3529. doi: 10.1021/acs.orglett.1c00937. Epub 2021 Apr 14.
In this project, a moderately efficient approach to multisubstituted -(isoquinolin-1-yl)sulfonamide derivatives was illustrated, utilizing -alkynylbenzaldoximes and zwitterionic ketenimine salts in a tandem reaction catalyzed by silver oxide. The oxophilicity of AgO, along with its nature as Lewis acid, pave the way for a smooth [3 + 2] cycloaddition between isoquinoline -oxides and ketenimine species, which is a key step in this reaction. DFT calculation suggests that 1,3-dipolar cycloaddition of nitrone and ketenimine proceeds through a selective stepwise mechanism.
在这个项目中，展示了一种利用银氧化物催化的串联反应，通过 - 炔基苯甲肟和两性离子烯酮亚胺盐合成多取代 - （异喹啉-1-基）磺酰胺衍生物的中效方法。AgO 的亲电性及其路易斯酸的性质为异喹啉氧化物和烯酮亚胺物种之间的[3 + 2]环加成反应铺平了道路，这是该反应的关键步骤。DFT 计算表明，硝酮和烯酮亚胺的 1,3-偶极环加成反应通过选择性逐步机制进行。
