Synthesis of 2,3-Dihydro-4-pyridones
and 4‑Pyridones
by the Cyclization Reaction of Ester-Tethered Enaminones
Posted on 2020-10-23 - 03:14
2,3-Dihydro-4-pyridone
skeleton is an important building block
in organic synthesis because it features several reaction sites with
nucleophilic or electrophilic properties. Herein, we disclose a method
for its formation by intramolecular cyclization of ester-tethered
enaminones, which can easily be synthesized from readily available
materials, such as amines, activated alkynes, and activated alkenes.
2,3-Dihydro-4-pyridones have been isolated in 41–90% yields.
We also demonstrate the transformation of these heterocycles into
another important class of compounds, 4-pyridones, by utilizing 2,3,5,6-tetrachloro-p-benzoquinone (chloranil) as an oxidizing agent. The latter
products were isolated in 65–94% yields.
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Stojanović, Milovan; Bugarski, Slobodan; Baranac-Stojanović, Marija (2020). Synthesis of 2,3-Dihydro-4-pyridones
and 4‑Pyridones
by the Cyclization Reaction of Ester-Tethered Enaminones. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.0c01537
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AUTHORS (3)
MS
Milovan Stojanović
SB
Slobodan Bugarski
MB
Marija Baranac-Stojanović