Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | 김원석 | * |
dc.date.accessioned | 2022-06-02T16:31:23Z | - |
dc.date.available | 2022-06-02T16:31:23Z | - |
dc.date.issued | 2022 | * |
dc.identifier.issn | 1615-4150 | * |
dc.identifier.other | OAK-31343 | * |
dc.identifier.uri | https://dspace.ewha.ac.kr/handle/2015.oak/261309 | - |
dc.description.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. | * |
dc.language | English | * |
dc.publisher | John Wiley and Sons Inc | * |
dc.subject | 2-pyridone derivatives | * |
dc.subject | Amrinone | * |
dc.subject | Continuous flow chemistry | * |
dc.subject | Milrinone | * |
dc.subject | Regioselective Suzuki-Miyaura reaction | * |
dc.subject | Selective halogen-lithium exchange | * |
dc.title | Protecting Group-Controlled Regioselective Synthesis for Unsymmetrical 3,5-Disubstituted Pyridones | * |
dc.type | Article | * |
dc.relation.issue | 8 | * |
dc.relation.volume | 364 | * |
dc.relation.index | SCIE | * |
dc.relation.index | SCOPUS | * |
dc.relation.startpage | 1440 | * |
dc.relation.lastpage | 1449 | * |
dc.relation.journaltitle | Advanced Synthesis and Catalysis | * |
dc.identifier.doi | 10.1002/adsc.202101514 | * |
dc.identifier.wosid | WOS:000770362200001 | * |
dc.identifier.scopusid | 2-s2.0-85126542258 | * |
dc.author.google | Kwon Y.-J. | * |
dc.author.google | Kim W.-S. | * |
dc.contributor.scopusid | 김원석(57203484044) | * |
dc.date.modifydate | 20240220102223 | * |