[1,5]-氢化物迁移引发的硼酸盐配合物脱烷基化环化反应生成 2-氧代-1,2,3,4-四氢喹啉-3-羧酸酯
[1,5]-Hydride Shift Triggered -Dealkylative Cyclization into 2-Oxo-1,2,3,4-tetrahydroquinoline-3-carboxylates via Boronate Complexes.
机构信息
Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, 117997 Moscow, Russia.
Institute of Translational Medicine, Pirogov Russian National Research Medical University, Ostrovitianov 1, 117997 Moscow, Russia.
出版信息
Molecules. 2022 Aug 18;27(16):5270. doi: 10.3390/molecules27165270.
A new simple one-pot two-step protocol for the synthesis of 2-oxo-1,2,3,4-tetrahydroquinoline-3-carboxylate from 2-(2-(benzylamino)benzylidene)malonate under the action of BF3·Et2O was developed. It was shown that the reaction proceeds through the formation of a stable iminium intermediate containing a difluoroboryl bridge in the dicarbonyl fragment of the molecule.
开发了一种新的简单一锅两步法，从 2-(2-(苯甲氨基)亚苄基)丙二酸酯在 BF3·Et2O 的作用下合成 2-氧代-1,2,3,4-四氢喹啉-3-羧酸酯。结果表明，该反应通过形成稳定的亚胺中间体进行，该中间体在分子的二羰基片段中含有一个二氟硼桥。
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