Further Insight into
the Castagnoli–Cushman-type
Synthesis of 1,4,6-Trisubstituted 1,6-Dihydropyridin-2-(3H)‑ones from 3‑Arylglutaconic Acid Anhydrides
posted on 2020-05-04, 10:44authored byAndrei Firsov, Olga Bakulina, Dmitry Dar’in, Natalia Guranova, Mikhail Krasavin
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.