利用硝基芳烃通过还原C - N偶联流线型合成4 -喹诺酮类药物

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2025-04-11 DOI:10.1002/adsc.202500393

Ni Dong, Xiao-Tian Zhang, Qin Tang, Jia-Xin Qian, Qi-Qi Luo, Long Cheng, Tian Cao, Xiang-Wei Liu

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引用次数: 0

摘要

喹诺酮类药物的合成是制备活性药物成分的关键技术。在这里，我们提出了一种步骤经济的方法，通过串联过程包括硝基芳烃的还原，aza - Michael加成和分子内Buchwald - Hartwig胺化来简化合成4 -喹诺酮类化合物。该策略使用合成的上游硝基芳烃作为可行的苯胺替代品，B2pin2作为有利的有机还原剂，以步骤经济的方式生产具有不同官能团的广泛的4 -喹诺酮类药物。该方案的潜在价值是通过后期将4 -喹诺酮部分安装到生物活性化合物上而突出的。

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Harnessing Nitroarenes in Streamlined Synthesis of 4‐Quinolones via Reductive C−N Coupling

The synthesis of quinolones is a key technology for the preparation of active pharmaceutical ingredients. Herein we present a step‐economical methodology for streamlined synthesis of 4‐quinolones from a tandem process involving a reduction of nitroarenes, an aza‐Michael addition and an intramolecular Buchwald‐Hartwig amination. This strategy uses synthetically upstream nitroarenes as viable aniline surrogates and B2pin2 as an enabling organic reductant, producing a wide range of 4‐quinolones bearing different functional groups in a step‐economical fashion. The potential value of this protocol is highlighted by late‐stage installation of 4‐quinolone moiety onto bioactive compounds.

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来源期刊

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.