2019/02/22 by A. V. Firsov, Evgeny Chupakhin, Dmitry Dar’in +2 · 22 citations
Biochemistry, Genetics and Molecular Biology · Chemistry · Pharmacology, Toxicology and Pharmaceutics · #Bioactive Compounds and Antitumor Agents #Chemistry #Combinatorial chemistry #Component (thermodynamics) #Marine Sponges and Natural Products #Medicinal chemistry #Organic chemistry #Synthesis and Biological Activity
paper · doi:10.1021/acs.orglett.9b00171
published in Organic Letters 21(6), 1637-1640 (American Chemical Society)
openalex publication_date 2019/02/22 · openalex created_date 2019/03/02 · openalex updated_date 2026/07/30
Attempted use of 3-arylglutaconic acids in the three-component version of the Castagnoli-Cushman reaction with amines and aromatic aldehydes resulted in an unexpected formation of 4,6-diaryl 1,6-dihydropyridine-2(3 H)-ones. These are of interest as representatives of a rare heterocyclic chemotype for de novo biological investigation. Alternatively, these compounds can be oxidized into their 2-pyridone counterparts, stereoselectively reduced to give cis-configured 4,6-diaryl 2-piperidones, or isomerized to 5,6-dihydropyridin-2(1 H)-ones. All the three scaffolds are well represented in the bioactive compound domain.