Successive Michael reactions on chromone derivatives with dimethyl 1,3-acetonedicarboxylate: one-pot synthesis of functionalized benzophenones, benzo[c]chromones and hydroxybenzoylfuroates |
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Authors: | Michael A. Terzidis Julia Stephanidou-Stephanatou Aristides Terzis Vassilis Psycharis |
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Affiliation: | a Department of Chemistry, Laboratory of Organic Chemistry, University of Thessaloniki, Thessaloniki 54124, Macedonia, Greece b X-Ray Laboratory, NCR ‘Democritos’, Athens, Greece |
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Abstract: | Chromones were reacted with dimethyl acetonedicarboxylate in the presence of DBU in THF at room temperature to furnish good yields of products, their structure depending on the substituent at 3-position. Unsubstituted chromones lead to methyl 7-hydroxy-6-oxo-6H-benzo[c]chromone-8-carboxylates 2, whereas by using 3-bromochromone, the methyl furoate 3c along with the unexpected furylcyclopropyl-chromene carboxylate 4c was isolated. Finally, from 3-formyl-chromones functionalized benzophenones 5 were isolated, in good yields. Plausible mechanisms are proposed. |
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Keywords: | Acetonedicarboxylate 3-Formyl-chromone Benzo[c]chromones Benzoyl-furoates |
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