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Dual Functionalization of the α,β-C–H Bonds in Alanine Ester Derivatives via Enamine–Imine Tautomerism: Construction of 4-Quinolinolate Skeletons through a Fragmentation–Reassembly Pathway
Organic Letters ( IF 4.9 ) Pub Date : 2024-12-16 , DOI: 10.1021/acs.orglett.4c04324
Jie Mao, Yue Hu, Shumiao He, Shuwei Zhang, Qiyuan Ma, Yu Yuan, Xiaodong Jia

Using a SbCl3/O2 mild oxidation system, a dual functionalization of the α,β-C–H bonds in alanine ester derivatives was achieved via enamine–imine tautomerism, and a series of quinoline-4-carboxylates were synthesized through a fragmentation–reassembly pathway. The investigation of the substrate scope revealed that various functional groups were easily tolerated, highlighting that this reaction provided an efficient path for the construction of the quinoline-4-carboxylate framework.

中文翻译:


通过 Enamine-亚胺互变异构作用实现丙氨酸酯衍生物中 α,β-C-H 键的双重功能化:通过碎裂-重组途径构建 4-喹啉酸骨架



使用 SbCl3/O2 轻度氧化系统,通过 enamine-亚胺互变异构实现了丙氨酸酯衍生物中 α,β-C-H 键的双重官能化,并通过碎裂-重组途径合成了一系列喹啉-4-羧酸盐。对底物范围的调查表明,各种官能团很容易耐受,突出表明该反应为构建喹啉-4-羧酸盐框架提供了有效的途径。
更新日期:2024-12-17
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