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.
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.
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.
Structure and stability relationship of 1,1 dimethyl 2 [β (α aroylstyryl)] derivatives
Al Hajjar,El Ezaby,El Rayyes
, p. 548 - 555 (1977)
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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.
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Croxall,Van Hook
, p. 2422,2424 (1949)
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Chemo- and regioselective preparation and reaction of a kinetic zinc enolate formed from a thiol ester and bis(iodozincio)methane
Ikeda, Zenichi,Hirayama, Takaharu,Matsubara, Seijiro
, p. 8200 - 8203 (2006)
(Chemical Equation Presented) Reactive functionalized enolates that are otherwise difficult to obtain can be prepared in a simple procedure by the treatment of a thiol ester with bis(iodozincio)methane in the presence of a palladium catalyst (see scheme). The terminal zinc enolates thus formed are kinetically controlled and react with a variety of electrophiles, such as aldehydes, ketones, and acyl cyanides. FG = functional group.
Preparation of 1,3-diketones by the reaction of bis(iodozincio)methene with acyl cyanides or palladium-catalyzed reaction with acyl chlorides
Matsubara, Seijiro,Kawamoto, Kazunari,Utimoto, Kiitiro
, p. 267 - 268 (1998)
Bis(iodozincio)methane, prepared from lead-catalyzed reaction of zinc with diiodomethane, afforded 1,3-diketones either by the reaction with acyl cyanides or by palladium catalyzed reaction with acyl chlorides. Reaction with adipoyl dichloride gave cyclic enol ester by intramolecular reaction.
Direct Access to 1,1-Dicarbonyl Sulfoxonium Ylides from Aryl Halides or Triflates: Palladium-Catalyzed Carbonylation
Yuan, Yang,Wu, Xiao-Feng
, p. 5310 - 5314 (2019)
The synthesis of 1,1-dicarbonyl sulfoxonium ylides by palladium-catalyzed carbonylation of aryl halides or triflates with α-carbonyl sulfoxonium ylides has been developed for the first time. This method provides a general approach to synthetically useful 1,1-dicarbonyl sulfoxonium ylides in high efficiency. The protocol displays a wide substrate scope, showing that the resulting 1,1-dicarbonyl sulfoxonium ylides have been converted into the corresponding 1,3-dicarbonyl compounds.
Lanthanoid complexes supported by retro-Claisen condensation products of β-triketonates
Abad Galán, Laura,Sobolev, Alexandre N.,Zysman-Colman, Eli,Ogden, Mark I.,Massi, Massimiliano
, p. 17469 - 17478 (2018)
β-Triketonates have been recently used as chelating ligands for lanthanoid ions, presenting unique structures varying from polynuclear assemblies to polymers. In an effort to overcome low solubility of the complexes of tribenzoylmethane, four β-triketones with higher lipophilicity were synthesised. Complexation reactions were performed for each of these molecules using different alkaline bases in alcoholic media. X-ray diffraction studies suggested that the ligands were undergoing decomposition under the reaction conditions. This is proposed to be caused by in situ retro-Claisen condensation reactions, consistent with two examples that have been reported previously. The lability of the lanthanoid cations in the presence of a varying set of potential ligands gave rise to structures where one, two, or three of the molecules involved in the retro-Claisen condensation reaction were linked to the lanthanoid centres. These results, along with measurements of ligand decomposition in the presence of base alone, suggest the solvent used will modulate the impact of the retro-Claisen condensation in these complexes.
The regioselective preparation of 1,3-diketones within a micro reactor
Wiles, Charlotte,Watts, Paul,Haswell, Stephen J.,Pombo-Villar, Esteban
, p. 1034 - 1035 (2002)
We demonstrate a simple method for the regioselective preparation of 1,3-diketones within a micro reactor from silyl enol ethers where the products are free from both competing O-acylation and diacylation products.
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Beak,Farney
, p. 4771 (1973)
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Formic acid reduction. XXIV. Path of the reductive fission of the centered β carbon bond of alkylidenebisketones
Suzuki,Sekiya
, p. 813 - 815 (1976)
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Bauld
, p. 2305 (1964)
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Br?nsted acid-catalyzed enantioselective addition of 1,3-diones to in situ generated N-acyl ketimines
Ray, Sumit K.,Sadhu, Milon M.,Singh, Vinod K.,Unhale, Rajshekhar A.
supporting information, p. 410 - 414 (2022/01/20)
A Br?nsted acid-catalyzed asymmetric Mannich-type addition of 1,3-diones to cyclic N-acyl ketimines is reported for the synthesis of enantioenriched isoindolinones. Various dicarbonyl-substituted isoindolinones bearing a quaternary carbon stereocenter were synthesized with excellent yields (up to 98%) and moderate to high enantioselectivities (up to 95% ee), and most of them possess a fluorine atom at the reactive center. Furthermore, the synthetic utility of the protocol has been demonstrated by the debenzoylation of the product.
Synthesis of Highly Substituted Biaryls by the Construction of a Benzene Ring via in Situ Formed Acetals
Balamurugan, Rengarajan,Manojveer, Seetharaman,Tarigopula, Chandrahas
, p. 11871 - 11883 (2021/09/13)
Herein, we present an interesting method for the construction of a benzene ring using propargylic alcohols and 1,3-dicarbonyls, which involves three new C-C bond formations via cascade alkylation, formylation, annulation, and aromatization to make substituted biaryls. This one-pot Br?nsted acid-promoted protocol utilizes the unique reactivity of the acetal formed under the reaction conditions. Alkynyl methyl ketones could be employed instead of 1,3-dicarbonyls as they are converted to 1,3-dicarbonyls by hydration under the reaction conditions.
