Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones
Abstract
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.
Keywords:
Hydrocarbons / Aromatic compounds / Organic compounds / Amines / CyclizationSource:
The Journal of Organic Chemistry, 2020, 85, 21, 13495-13507Publisher:
- American Chemical Society (ACS)
Funding / projects:
DOI: 10.1021/acs.joc.0c01537
ISSN: 0022-3263; 1520-6904
PubMed: 33092340
WoS: 000589941700010
Scopus: 2-s2.0-85095834928
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Institution/Community
IHTMTY - JOUR AU - Stojanović, Milovan AU - Bugarski, Slobodan AU - Baranac-Stojanović, Marija PY - 2020 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/4020 AB - 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. PB - American Chemical Society (ACS) T2 - The Journal of Organic Chemistry T1 - Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones VL - 85 IS - 21 SP - 13495 EP - 13507 DO - 10.1021/acs.joc.0c01537 ER -
@article{ author = "Stojanović, Milovan and Bugarski, Slobodan and Baranac-Stojanović, Marija", year = "2020", abstract = "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.", publisher = "American Chemical Society (ACS)", journal = "The Journal of Organic Chemistry", title = "Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones", volume = "85", number = "21", pages = "13495-13507", doi = "10.1021/acs.joc.0c01537" }
Stojanović, M., Bugarski, S.,& Baranac-Stojanović, M.. (2020). Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones. in The Journal of Organic Chemistry American Chemical Society (ACS)., 85(21), 13495-13507. https://doi.org/10.1021/acs.joc.0c01537
Stojanović M, Bugarski S, Baranac-Stojanović M. Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones. in The Journal of Organic Chemistry. 2020;85(21):13495-13507. doi:10.1021/acs.joc.0c01537 .
Stojanović, Milovan, Bugarski, Slobodan, Baranac-Stojanović, Marija, "Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones" in The Journal of Organic Chemistry, 85, no. 21 (2020):13495-13507, https://doi.org/10.1021/acs.joc.0c01537 . .