Synthesis of 4-hydroxy-3-benzoylpyridin-2(1H)-one derivatives using pyrrolidine as catalyst

• Published in: Synthetic communications Vol. 53; no. 6; pp. 492 - 502
• Main Authors: Li, Linbo, Liu, Yuxiao, Zhou, Shujing, Li, Jinjing, Qi, Chenze, Zhang, Furen
• Format: Journal Article
• Language: English
• Published: PHILADELPHIA Taylor & Francis 19.03.2023; Taylor & Francis Ltd
• Subjects: 3-Benzoylpyridin-2(1H)-one derivatives;β-nitrostyrenes; Chemical synthesis; Chemistry; Chemistry, Organic; Ethanol; Physical Sciences; pyridinone; pyrrolidine; Science & Technology; Substrates; synthesis; beta-nitrostyrenes; synthesis; DOMINO REACTION; THIOUREA; pyrrolidine; ORGANOCATALYST; PYRIDINES; PYRAZOLOPYRIDINE DERIVATIVES; MICHAEL ADDITION; MILD; pyridinone; 3-Benzoylpyridin-2(1H)-one derivatives; AEROBIC OXIDATION; INHIBITORS; EFFICIENT
• ISSN: 0039-7911; 1532-2432
• DOI: 10.1080/00397911.2023.2177872

A facile synthesis of novel 3-functionalized pyridine derivatives has been accomplished through the reaction of 4-hydroxy-3-benzoylpyridin-2(1H)-ones and β-nitrostyrenes in the presence of catalytic amount of pyrrolidine (10 mol%). In this process, the desired products were obtained with 72-87% yields using ethanol as solvent at 80 °C for 4 h. In addition, a total of 19 examples were obtained, which exhibited the broad substrate scope of the transformation. The reaction process may involve the formation of an unstable enamine intermediate and then undergo hydrolysis to afford 4-hydroxy-3-benzoylpyridin-2(1H)-one derivatives.