Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.
J Org Chem. 2020 May 15;85(10):6822-6829. doi: 10.1021/acs.joc.0c00836. Epub 2020 May 4.
The earlier reported three-component Castagnoli-Cushman-type synthesis of 1,4,6-trisubstituted 1,6-dihydropyridin-2-(3)-ones from 3-arylglutaconic acids, primary amines, and aromatic aldehydes has been further investigated. It was shown to proceed via 3-arylglutaconic anhydrides, which, in turn, were found to give superior results in the two-component reactions with imines. The initial formation of the Castagnoli-Cushman carboxylic acids was shown to be the case, and their decarboxylation was found to follow a complex, "forked" pathway, which was confirmed by deuterium incorporation experiments.
早期报道的三组分 Castagnoli-Cushman 型合成法，可从 3-芳基戊二酰酸、伯胺和芳香醛制备 1,4,6-三取代的 1,6-二氢吡啶-2-(3)-酮，我们对其进行了进一步研究。研究表明该反应经过 3-芳基戊二酰酸酐，在与亚胺的二组分反应中，发现其结果更优。我们证明了 Castagnoli-Cushman 羧酸的最初形成情况，且其脱羧遵循复杂的“叉型”途径，氘掺入实验对此进行了证实。
