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.
TY - 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 . .
