Further Insight into the Castagnoli-Cushman-type Synthesis of 1,4,6-Trisubstituted 1,6-Dihydropyridin-2-(3H)-ones from 3-Arylglutaconic Acid Anhydrides.

Andrei Firsov, Olga Bakulina, Dmitry Dar'in, Natalia Guranova, Mikhail Krasavin

The Journal of organic chemistry 2020 May 15

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The earlier reported three-component Castagnoli-Cushman-type synthesis of 1,4,6-trisubstituted 1,6-dihydropyridin-2-(3H)-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.

Citation

Andrei Firsov, Olga Bakulina, Dmitry Dar'in, Natalia Guranova, Mikhail Krasavin. Further Insight into the Castagnoli-Cushman-type Synthesis of 1,4,6-Trisubstituted 1,6-Dihydropyridin-2-(3H)-ones from 3-Arylglutaconic Acid Anhydrides. The Journal of organic chemistry. 2020 May 15;85(10):6822-6829