Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory 1, Moscow 119991 Russia.
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Street, Irkutsk 664033, Russia.
J Org Chem. 2020 Aug 7;85(15):9993-10006. doi: 10.1021/acs.joc.0c01277. Epub 2020 Jul 20.
The reaction of quinolines with CF-ynones resulted in the formation of 1,3-oxazinoquinolines. Subsequent treatment of the reaction mixture with a base initiated deep structural transformation of primary products. Both steps proceed in very high yield. As a result, unusual rearrangement of 1,3-oxazinoquinolines to form either 2-arylquinolines or 2-aryl-3-trifluoroacetylquinolines was discovered. The decisive role of the base in the reaction direction was shown. Using these reactions, highly efficient pathways to 2-arylquinolines and 2-aryl-3-trifluoroacetylquinolines were elaborated to provide the corresponding compounds in high yields using a simple one-pot procedure. The possible mechanism of rearrangement is discussed.
喹啉与 CF-ynones 的反应生成了 1,3-恶嗪并喹啉。随后，用碱处理反应混合物，引发了初级产物的深度结构转化。这两个步骤都以非常高的产率进行。结果，发现了 1,3-恶嗪并喹啉的不寻常重排，形成 2-芳基喹啉或 2-芳基-3-三氟乙酰基喹啉。还表明了碱在反应方向中的决定性作用。使用这些反应，可以通过简单的一步法以高收率得到相应的化合物，从而精心设计了高效的 2-芳基喹啉和 2-芳基-3-三氟乙酰基喹啉的合成途径。讨论了重排的可能机制。
