120-46-7Relevant articles and documents
Palladium-catalysed addition of potassium phenyltrifluoroborate to dinitriles: Synthesis of diketone compounds
Wang, Xingyong,Wang, Qingzong,Chen, Jiuxi,Liu, Miaochang,Ding, Jinchang,Wu, Huayue
, p. 470 - 472 (2013)
Pd(OAc)2/1,10-phenanthroline-catalysed addition of potassium phenyltrifluoroborate to aliphatic dinitriles in 2-MeTHF has been developed, achieving diphenyl diones in moderate to excellent yields. The scope of the developed approach was successfully explored toward the addition of potassium phenyltrifluoroborate to aromatic dinitriles. Additionally, a plausible pathway for the formation of the diones has been proposed.
Kinetics of the substitution of β-Diketones in β-diketonato(1,5-cyclooctadiene)rhodium(I) complexes by benzoyl-1,1,1-trifluoroacetone
Potgieter, J. H.
, p. 369 - 376 (1989)
The kinetics and mechanism of the reactions between and trifluorobenzoylacetone (TFBA) to give have been studied in a petroleum-ether medium at various temperatures with UV spectroscopy.The rate law is -d/dt=(ks+ky) and the reaction is shown to proceed via an associative mechanism.The value of ks and ky were determined for various β-diketone complexes with β-diketone=acac, BA, DBM, TFAA and HFAA.The reactivities of the complexes fall as the β-diketone is varied in the sequence BA>acac>DBM>TFAA>HFAA, indicating that electronegative substituents in the β-diketone increase the trans-effect and therefore the strength of the Rh-O bonds.Since the ring opening is the rate-determining step in the reaction.It can be concluded that the complex containing the β-diketone with the largest trans-effect, which gives rise to the strongest Rh-O bonds, will undergo the slowest substitution.The effect of the substituents of the β-diketone (CF3, phenyl and CH3) on the trans-effect is discussed.
An alternative route to 1,3-diketones promoted by samarium diiodide
Ying, Taokai,Bao, Weiliang,Zhang, Yongmin,Xu, Weinming
, p. 3885 - 3886 (1996)
Sml2 promoted condensation of α-haloketones with carboxylic acid chlorides or anhydrides leads to 1,3-diketones.
Copper-catalyzed domino synthesis of 2-imino-1H-imidazol-5(2H)-ones and Quinoxalines involving C-C bond cleavage with a 1,3-dicarbonyl unit as a leaving group
Yang, Yan,Ni, Fan,Shu, Wen-Ming,Wu, An-Xin
, p. 11776 - 11782 (2014)
Although 2-imino-1H-imidazol-5(2H)-ones have important biological activities in metabolism, their synthesis has rarely been investigated. Quinoxalines as privileged scaffolds in medicinal chemistry have been extensively investigated, but the development of novel and efficient synthetic methods remains very attractive. Herein, we have developed two copper-catalyzed domino reactions for the synthesis of 2-imino-1H-imidazol-5(2H) -ones and quinoxalines involving C-C bond-cleavage with a 1,3-dicarbonyl unit as a leaving group. The domino sequence for the synthesis of 2-imino-1H-imidazol- 5(2H)-ones includes aza-Michael addition, intramolecular cyclization, C-C bond-cleavage, 1,2-rearrangement, and aerobic dehydrogenation reaction, whereas the domino sequence for the synthesis of quinoxalines includes aza-Michael addition, intramolecular cyclization, elimination reaction, and C-C bond-cleavage reaction. The two domino reactions have significant advantages including high efficiency, mild reaction conditions, and high tolerance of various functional groups.
A novel synthesis of 1,3-diketones by reaction of an α-bromoketone with acyl chlorides promoted by gallium triiodide
Chen, Rener,Wu, Huayue,Zhang, Yongmin
, p. 666 - 667 (1999)
Promoted by gallium triiodide, an α-bromoketone, bromomethyl phenyl ketone, is treated with acyl chlorides to synthesize 1,3-diketones in good yields under mild and neutral conditions.
STRUCTURE OF THE PRODUCTS OF THE REACTION OF 5,6-DIAMINO-1,3-DIMETHYLURACIL WITH 1,3-DIARYL-2,3-DIHALOPROPANONES
Kolos, N. N.,Shishkin, O. V.,Orlov, V. D.,Struchkov, Yu. T.
, p. 485 - 491 (1995)
The reaction of 5,6-diamino-1,3-dimethyluracil with α,β-dihalopropanones gives only β-(5-imino-6-amino-1,3-uracil)chalcones.An x-ray diffraction structural analysis was carried out for one of these products.
Synthesis and application of 2,6-dicarboxy pyridinium fluorochromate as a new solid-phase oxidant
Tajbakhsh,Hosseinzadeh,Sadatshahabi
, p. 1547 - 1554 (2005)
2,6-Dicarboxypyridinium fluorochromate (2,6-DCPFC) was prepared and used for oxidation of alcohols, phenols, and hydroquinones under solvent-free conditions. This new compound is more efficient and has certain advantages over similar oxidizing agents in terms of the amount of oxidant, lack of solvent, short reaction times, and high yields. Copyright Taylor & Francis, Inc.
β-Diketone synthesis by reaction of α-haloketones with acid chlorides or acid anhydrides promoted by samarium triiodide
Ying, TaoKai,Bao, Weiliang,Zhang, Yongmin
, p. 2905 - 2909 (1996)
Promoted by SmI3, α-haloketones were reacted with acid chlorides or acid anhydrides and β-diketones were synthesized via intermediate samarium enolates.
Enamines as Surrogates of Alkene Carbanions for the Reductive Alkenylation of Secondary Amides: An Approach to Allylamines
Wang, Ai-E,Yu, Cun-Cun,Chen, Ting-Ting,Liu, Yong-Peng,Huang, Pei-Qiang
, p. 999 - 1002 (2018)
A new strategy to construct allylamines through reductive alkenylation of secondary amides with enamines is reported. The method features the use of trifluoromethanesulfonic anhydride as an activation reagent of amides, and enamines as unconventional alkenylation reagents. In this manner, enamines serve as surrogates of alkene carbanions instead of the classical enolates equivalents. A possible mechanism involving a Hoffmann-like elimination of the amine-borane complex intermediate is proposed.
Acylsilanes and C-Stannylimines as Anion Equivalents
Degl'Innocenti, Alessandro,Pike, Stephen,Walton, David R. M.,Seconi, Giancarlo,Ricci, Alfredo,Fiorenza, Mariella
, p. 1201 - 1202 (1980)
Acylsilanes and C-stannylimines react with organic halides in the presence of KF-18-crown-6 ether to give ketones and ketimines, respectively.
