取代吡啶/吡啶并[3,2-c]香豆素的取代基导向合成：α-H和甲基/芳基取代肟乙酸酯与3-甲酰基色酮的连续反应
Substituent-Oriented Synthesis of Substituted Pyridines/Pyrido[3,2-C]coumarins Sequential Reactions of α-H and Me/Aryl Substituted Oxime Acetates and 3-Formylchromones.
作者信息
Bodala Varaprasad, Podugu Rajitha Lakshmi, Yettula Kumari, Kadiri Sunanda Kumari, Vidavalur Siddaiah
机构信息
Department of Organic Chemistry and FDW, School of Chemistry, AU College of Science and Technology, Andhra University, Visakhapatnam, India, 500003.
Department of MicrobiologyAndhra University, AU College of Science and Technology, Andhra University, Visakhapatnam, India, 530003.
出版信息
J Org Chem. 2024 Sep 20;89(18):12957-12966. doi: 10.1021/acs.joc.4c00899. Epub 2024 Aug 28.
A facile one pot sequential and highly chemoselective synthesis of substituted pyridines/pyrido[3,2-]coumarins has been developed from oxime acetates and 3-formylchromones in the presence of FeCl. 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-]coumarins were formed via intermolecular Michael addition. Besides, anti-TB activity was screened for some of the synthesized pyridines. Among the tested compounds, , , , , , , and were found to have good activity with an MIC of 12.5 μg/mL.
在氯化铁存在下，已开发出一种简便的一锅法顺序且高度化学选择性的合成取代吡啶/吡啶并[3,2 -]香豆素的方法，该方法以肟乙酸酯和3 - 甲酰基色酮为原料。此反应受肟乙酸酯α位（氢、甲基/芳基）上不同取代基的导向。机理研究表明，取代吡啶是通过分子内氮杂迈克尔加成随后开环形成的，而吡啶并[3,2 -]香豆素是通过分子间迈克尔加成形成的。此外，还对一些合成的吡啶进行了抗结核活性筛选。在测试的化合物中，发现[具体化合物]具有良好的活性，最低抑菌浓度为12.5μg/mL。
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