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Protecting Group-Controlled Regioselective Synthesis for Unsymmetrical 3,5-Disubstituted Pyridones
- Title
- Protecting Group-Controlled Regioselective Synthesis for Unsymmetrical 3,5-Disubstituted Pyridones
- Authors
- Kwon Y.-J.; Kim W.-S.
- Ewha Authors
- 김원석
- SCOPUS Author ID
- 김원석
- Issue Date
- 2022
- Journal Title
- Advanced Synthesis and Catalysis
- ISSN
- 1615-4150
- Citation
- Advanced Synthesis and Catalysis vol. 364, no. 8, pp. 1440 - 1449
- Keywords
- 2-pyridone derivatives; Amrinone; Continuous flow chemistry; Milrinone; Regioselective Suzuki-Miyaura reaction; Selective halogen-lithium exchange
- Publisher
- John Wiley and Sons Inc
- Indexed
- SCIE; SCOPUS
- Document Type
- Article
- Abstract
- Protecting group-controlled regioselective functionalization of 3,5-dibromo-2-pyridones has been studied for preparation of unsymmetrical 3,5-disubstituted 2-pyridones. A bulky di-tert-butyl(isobutyl)silyl (BIBS) group was utilized for C5 regioselective arylation in Suzuki-Miyaura reactions. Meanwhile, the p-toluenesulfonyl (Ts) group was used to maximize C3 selective halogen-lithium exchange employing flow chemistry. Most of the reactions proceeded well, with yields of 76 to 95% and excellent regioselectivity. A one-pot synthesis of unsymmetrical 3,5-diaryl-2-pyridones starting from 3,5-dibromo-2-silyloxypyridine was conducted to demonstrate the practical convenience. Further functionalization onto the remaining bromine group, such as transition metal-catalyzed C−C and C−N bond-forming reactions and retro-Brook rearrangement for C−Si bond formation, was accomplished for synthesis of biologically relevant 3,5-disubstituted 2-pyridones. Finally, amrinone and milrinone, commonly used for congestive heart failure, were synthesized in three steps from 3,5-dibromo-2-pyridones in 41% and 56% overall yields, respectively. (Figure presented.). © 2022 Wiley-VCH GmbH.
- DOI
- 10.1002/adsc.202101514
- Appears in Collections:
- 자연과학대학 > 화학·나노과학전공 > Journal papers
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