Scaffold Hopping of Pyrimidines into 2-Acylpyrroles

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-14 DOI:10.1021/acs.orglett.6c03859

Enxian Li,Cong Lv,Shunyao Huang,Yonglin Shi,Shenxiang Wang,Weichao Xue,Xueli Zheng,Hua Chen,Ruixiang Li,Haiyan Fu

引用次数: 0

Abstract

Abstract A practical skeletal-editing strategy was developed for the conversion of 4-substituted pyrimidines into 2-acyl-5-arylpyrroles. The transformation directly converts a six-membered, electron-deficient pyrimidine into a five-membered azole while simultaneously installing an acyl group. The reaction sequence involves pyrimidine activation, ring-opening, fragmentation, and ring reconstruction. Central to this strategy is the controlled generation of pyrimidine-derived vinamidinium salts as open-chain A4 synthons, which are then intercepted by α-bromoketones as functionalized annulation reagents. The developed scaffold-hopping method can be applied for late-stage modification of pyrimidine-containing bioactive or pharmaceutical molecules.

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嘧啶支架跳跃成2-酰基吡咯

摘要：开发了一种实用的骨架编辑策略，用于将4-取代嘧啶转化为2-酰基-5-芳基吡咯。这种转化直接将六元缺电子嘧啶转化为五元唑，同时加入酰基。反应顺序包括嘧啶活化、开环、断裂和环重建。该策略的核心是控制生成嘧啶衍生的vinamidinium盐作为开链A4合成子，然后被α-溴酮作为功能化环化试剂拦截。该方法可用于含嘧啶生物活性分子或药物分子的后期修饰。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.