Firsov Andrei, Chupakhin Evgeny, Dar'in Dmitry, Bakulina Olga, Krasavin Mikhail
Saint Petersburg State University , Saint Petersburg 199034 , Russian Federation.
Immanuel Kant Baltic Federal University , Kaliningrad 236016 , Russian Federation.
Org Lett. 2019 Mar 15;21(6):1637-1640. doi: 10.1021/acs.orglett.9b00171. Epub 2019 Feb 22.
Attempted use of 3-arylglutaconic acids in the three-component version of the Castagnoli-Cushman reaction with amines and aromatic aldehydes resulted in an unexpected formation of 4,6-diaryl 1,6-dihydropyridine-2(3 H)-ones. These are of interest as representatives of a rare heterocyclic chemotype for de novo biological investigation. Alternatively, these compounds can be oxidized into their 2-pyridone counterparts, stereoselectively reduced to give cis-configured 4,6-diaryl 2-piperidones, or isomerized to 5,6-dihydropyridin-2(1 H)-ones. All the three scaffolds are well represented in the bioactive compound domain.
尝试在与胺类和芳香醛的卡斯塔尼奥利 - 库什曼反应的三组分反应中使用3 - 芳基戊二酸，结果意外地生成了4,6 - 二芳基 - 1,6 - 二氢吡啶 - 2(3H)-酮。作为一种罕见的杂环化学类型的代表，这些化合物对于全新的生物学研究具有重要意义。另外，这些化合物可以被氧化为它们的2 - 吡啶酮类似物，立体选择性还原得到顺式构型的4,6 - 二芳基 - 2 - 哌啶酮，或者异构化为5,6 - 二氢吡啶 - 2(1H)-酮。这三种骨架在生物活性化合物领域都有很好的体现。
