Straightforward Synthesis of 2(5H)-Furanones as Promising Cross-Coupling Partners: Direct Furanone Annulation Utilizing Ti-Mediated Aldol Addition
نویسندگان
چکیده
Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating mor p-bromoand p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)furanone pharmacore. The present one-pot annulation method involves two distinctive reactions: (i) a powerful and crossed Ti-direct aldol addition and (ii) an acid-induced characteristic cyclocondensation, leading to 2(5H)-furanones. Suzuki-Miyaura cross-coupling of 5-(4-bromophenyl)furan-2(5H)-ones, 5-(4-tosyloxyphenyl)-3,4-dimethylfuran-2(5H)-ones and a furan derivative successfully afforded the corresponding products with the 2(5H)-furanone skeleton.
منابع مشابه
Organocatalytic asymmetric direct vinylogous aldol reactions of γ-crotonolactone with aromatic aldehydes.
The direct aldol reaction of γ-crotonolactone and various aromatic aldehydes is catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts to provide diastereomerically and enantiomerically enriched 5-substituted 2(5H) furanones (γ-butenolides). The reaction is a simple alternative to the classical vinylogous aldol reaction of silyloxy furans.
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