以取代基为导向，通过 α-H 和 Me/Aryl 取代的肟醋酸酯与 3-Formylchromones 的顺序反应合成取代的吡啶/吡啶并[3,2-C]香豆素。

IF 3.6 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2024-09-20 Epub Date: 2024-08-28 DOI:10.1021/acs.joc.4c00899

Varaprasad Bodala, Rajitha Lakshmi Podugu, Kumari Yettula, Sunanda Kumari Kadiri, Siddaiah Vidavalur

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引用次数: 0

摘要

在 FeCl2 的存在下，以肟类醋酸盐和 3-甲酰基色酮为原料，开发了一种简便的一锅顺序高化学选择性合成取代吡啶/吡啶并[3,2-c]香豆素的方法。肟醋酸盐的 α 位（H、甲基/芳基）上的不同取代基引导了这一反应。机理研究表明，取代的吡啶是通过分子内的氮杂迈克尔加成，然后开环形成的，而吡啶并[3,2-c]香豆素则是通过分子间迈克尔加成形成的。此外，还对合成的一些吡啶进行了抗结核活性筛选。在测试的化合物中，发现 3ga、3ha、3ja、3ma、3ac、4pa、4pb 和 4sb 具有良好的活性，其 MIC 为 12.5 μg/mL。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Substituent-Oriented Synthesis of Substituted Pyridines/Pyrido[3,2-C]coumarins via Sequential Reactions of α-H and Me/Aryl Substituted Oxime Acetates and 3-Formylchromones.

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Substituent-Oriented Synthesis of Substituted Pyridines/Pyrido[3,2-C]coumarins via Sequential Reactions of α-H and Me/Aryl Substituted Oxime Acetates and 3-Formylchromones.

A facile one pot sequential and highly chemoselective synthesis of substituted pyridines/pyrido[3,2-c]coumarins has been developed from oxime acetates and 3-formylchromones in the presence of FeCl₂. This reaction was oriented by different substituents on the α-position (H, methyl/aryl) of oxime acetates. Mechanistic investigations suggested that substituted pyridines were formed via intramolecular aza-Michael addition followed by ring opening, while pyrido[3,2-c]coumarins were formed via intermolecular Michael addition. Besides, anti-TB activity was screened for some of the synthesized pyridines. Among the tested compounds, 3ga, 3ha, 3ja, 3ma, 3ac, 4pa, 4pb and 4sb were found to have good activity with an MIC of 12.5 μg/mL.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.