72610-53-8Relevant academic research and scientific papers
Organophosphane-Promoted Synthesis of Functionalized α,β-Unsaturated Alkenes and Furanones via Direct β-Acylation
Liou, Yan-Cheng,Su, Yin-Hsiang,Ku, Kuan-Chun,Edukondalu, Athukuri,Lin, Chun-Kai,Ke, You-Syuan,Karanam, Praneeth,Lee, Chia-Jui,Lin, Wenwei
supporting information, p. 8339 - 8343 (2019/10/16)
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.
Synthesis and tubulin-binding properties of non-symmetrical click C5-curcuminoids
Caldarelli, Antonio,Penucchini, Eleonora,Caprioglio, Diego,Genazzani, Armando A.,Minassi, Alberto
, p. 5510 - 5517 (2013/09/02)
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
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
Olekhnovich,Arsen'ev,Borodkin,Korobka,Olekhnovich
, p. 1160 - 1166 (2007/10/03)
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
Reactions of β-Diketones with Aromatic Aldehydes and Ketones in the Presence of Potassium Hydride
Rathman, Terry L.,Greenwood, Thomas D.,Wolfe, James F.
, p. 1086 - 1091 (2007/10/02)
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).
