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Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones

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2020
Authors
Stojanović, Milovan
Bugarski, Slobodan
Baranac-Stojanović, Marija
Article (Published version)
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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 / Cyclization
Source:
The Journal of Organic Chemistry, 2020, 85, 21, 13495-13507
Publisher:
  • American Chemical Society (ACS)
Projects:
  • Ministry of Education, Science and Technological Development, Republic of Serbia, Grant no. 451-03-68/2020-14/200168 (University of Belgrade, Faculty of Chemistry) (RS-200168)

DOI: 10.1021/acs.joc.0c01537

ISSN: 0022-3263; 1520-6904

PubMed: 33092340

WoS: 000589941700010

Scopus: 2-s2.0-85095834928
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URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4020
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