- Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation
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We report a phosphine-mediated direct β-acylation of α,β-unsaturated 1,3-diketones with acyl chlorides and a base. Functionalized furanones were also prepared by the reaction of cinnamic acid and acyl chloride according to our protocol via β-acylation. Our studies revealed that α,β-unsaturated 1,3-diketones with an electron-donating group at the second position favor the formation of β-acylated products, whereas those with oxygen, such as anhydrides, favor furanones via an unprecedented C-acylation/cyclization sequence.
- Liou, Yan-Cheng,Su, Yin-Hsiang,Ku, Kuan-Chun,Edukondalu, Athukuri,Lin, Chun-Kai,Ke, You-Syuan,Karanam, Praneeth,Lee, Chia-Jui,Lin, Wenwei
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supporting information
p. 8339 - 8343
(2019/10/16)
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- Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids
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A click-type entry into shortened curcuminoids of the diarylpentanoid type has been developed. The reaction is ideally suited to generate non-symmetrical analogues of curcumin, a class of natural products difficult to access but of growing biomedical rele
- Caldarelli, Antonio,Penucchini, Eleonora,Caprioglio, Diego,Genazzani, Armando A.,Minassi, Alberto
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p. 5510 - 5517
(2013/09/02)
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- Acetals and Vinyl Ethers of Unsaturated Aldehydes and Ketones in New Syntheses of Heterocyclic Compounds. VII. Boundary Conditions of Formation of 1,3-Dioxenilium Salts
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Factors governing the limiting conditions of the 1,3-dioxenilium salts formation are the structure of 1,3-ketoenol favorable for stabilization of its protonated form, low basicity and weak enolization of the ketone. The most effective condensation catalys
- Olekhnovich,Arsen'ev,Borodkin,Korobka,Olekhnovich
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p. 1160 - 1166
(2007/10/03)
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- Reactions of β-Diketones with Aromatic Aldehydes and Ketones in the Presence of Potassium Hydride
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Reaction of benzoylacetone (1a) and acetylacetone (1b) with benzophenone in the presence of excess potassium hydride affords terminal aldol condensation products 5-hydroxy-1,5,5-triphenyl-1,3-pentanedione (3) and 6-hydroxy-6,6-diphenyl-2,4-hexanedione (9), respectively.Potassium hydride promoted reactions of 1a with p-anisaldehyde and p-tolualdehyde result in formation of tetraketones 1,9-diphenyl-5-(p-methoxyphenyl)-1,3,7,9-nonanetetrone (5a) and 1,9-diphenyl-5-(p-tolyl)-1,3,7,9-nonanetetrone (5b), respectively.Evidence is presented to support formation of 5a and 5b via a sequence of reactions involving Michael addition of the dianion of 1a to the monoanion of the unsaturated β-diketones derived from terminal aldol condensation of the respective aldehydes with the dianion of 1a.Reaction of 1b with p-tolualdehyde under similar conditions yields mainly 1,7-bis(p-tolyl)-1,6-heptadiene-3,5-dione (10).Reaction of 1b with the monoanion of 1-phenyl-5-(p-methoxyphenyl)-4-pentene-1,3-dione (2b) in the presence of excess potassium hydride affords the novel hexaketone 1,15-diphenyl-5,11-bis(p-methoxyphenyl)-1,3,7,9,13,15-pentadecanehexone (18).
- Rathman, Terry L.,Greenwood, Thomas D.,Wolfe, James F.
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p. 1086 - 1091
(2007/10/02)
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