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

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters 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

引用次数: 0

Abstract

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.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.