Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones
| Autor: | Milovan Stojanović, Slobodan Bugarski, Marija Baranac-Stojanović |
|---|---|
| Rok vydání: | 2020 |
| Předmět: |
Aromatic compounds
010405 organic chemistry Organic Chemistry Intramolecular cyclization Chloranil 010402 general chemistry 01 natural sciences Combinatorial chemistry Hydrocarbons 0104 chemical sciences chemistry.chemical_compound chemistry Nucleophile Cyclization Organic compounds Electrophile Oxidizing agent Organic synthesis Amines |
| Zdroj: | The Journal of Organic Chemistry |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.0c01537 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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