Mild acetalisation of mono and dicarbonyl compounds catalysed by titanium tetrachloride. Facile synthesis of β-keto enol ethers

Clerici, Angelo; Pastori, Nadia; Porta, Ombretta

doi:10.1016/s0040-4020(00)01001-2

Cited by 86 publications

(51 citation statements)

References 29 publications

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“…Our previous investigations [12,22] on the acetalization of various classes of aldehydes under catalysis by TiCl 4 /Et 3 N (or NH 3 ) in MeOH revealed interesting opportunities for the chemoselective protection of the more reactive aromatic aldehydes in situ, while the TiCl 3 /NH 3 system reduces the unprotected aromatic ketones to alcohol [Equation (2)]. In fact, when an equimolar mixture of an aromatic ketone and an aromatic aldehyde (5 mmol each) was allowed (2) to react with a catalytic amount of TiCl 4 (1 mol %) and Et 3 N for 15 min in 20 mL of MeOH, and then treated with aqueous ammonia followed by TiCl 3 addition (10 mmol), a very selective reaction occurred.…”

Section: Intermolecular Chemoselective Reductions Of Aldehydes And/ormentioning

confidence: 99%

Facile Reduction of Aromatic Aldehydes, Ketones, Diketones and Oxo Aldehydes to Alcohols by an Aqueous TiCl3/NH3 System: Selectivity and Scope

Clerici¹,

Pastori²,

Porta³

2002

Eur. J. Org. Chem.

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A simple and rapid procedure for the almost quantitative reduction of aromatic aldehydes, ketones, diketones and oxo aldehydes to alcohols by use of TiCl 3 /NH 3 in aqueous methanol solution is reported. The reducing system distinguishes between different classes of aldehydes and/or ketones, and many functionalities that usually do not survive under reducing conditions are tolerated well. The concept of reversal

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Section: Intermolecular Chemoselective Reductions Of Aldehydes And/ormentioning

confidence: 99%

Facile Reduction of Aromatic Aldehydes, Ketones, Diketones and Oxo Aldehydes to Alcohols by an Aqueous TiCl3/NH3 System: Selectivity and Scope

Clerici¹,

Pastori²,

Porta³

2002

Eur. J. Org. Chem.

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“…General Procedures for 3-(4-Halophenyl)-3-oxopropane (1-3) 15) 1-(4-Halophenyl)ethanone (0.05 mol) was dissolved in dry THF or toluene, and stirred in the ice bath. Sodium (0.075 mol) was added to the solution, the mixture was stirred for 30 min in the ice bath.…”

Section: Design Synthesis and Biological Evaluation Of 3-(4-halophenmentioning

confidence: 99%

Design, Synthesis and Biological Evaluation of 3-(4-Halophenyl)-3-oxopropanal and Their Derivatives as Novel Antibacterial Agents

Liu

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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In continuing our program aimed to search for potent drugs for bacterial infections, a series of 3-(4-halophenyl)-3-oxopropanal and their derivatives were designed, synthesized and their antibacterial activities in vitro against both Gram-positive bacteria Staphylococcus aureus and Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa were evaluated. Compounds 7, 8, 13-16, 21 and 22 had moderate antibacterial activities against Staphylococcus aureus (minimal inhibitory concentration (MIC) Ͻ16 mg/ml), suggesting that the introduction of mono-methoxyamine or ethoxyamine moiety might play an important role in determining the potent antibacterial activities. Furthermore, the antibacterial activities of select compounds 7, 15 and 16 against the clinically important pathogenic bacteria-methicillin-resistant Staphylococcus aureus (MRSA) were also investigated. Results showed that these compounds exhibited more potent activities than the well-known antibacterial agents Houttuynin and Levofloxacin.

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“…It is noteworthy that the reaction of propargyl alcohol (Entry 7) and allyl alcohol (Entry 10) underwent smoothly with dimedone giving excellent yields of the -keto enol ethers 7 and 10, respectively. We have also successfully deprotected 14 the -keto enol ethers (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) to the corresponding cyclic -diketones in good …”

mentioning

confidence: 99%

“…These open chain -diketones preferably exist in cis-enol form in the solution and serve as bidentate ligands which may form a stable cerium complex. 6 In contract, enolization of cyclic -diketones forms fixed trans-enols where no such complex formation is sterically possible. In summary, we have developed a mild and efficient CAN-catalyzed method for the synthesis of -keto enol ethers from -diketones at room temperature in good to excellent yields.…”

mentioning

confidence: 99%

Cerium(IV) Ammonium Nitrate-catalyzed Synthesis of β-Keto Enol Ethers from Cyclic β-Diketones and Their Deprotection

Banerjee¹,

Mandal²,

Roy³

2005

Chemistry Letters

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A mild and efficient method for etherification of cyclic -diketones with alcohols has been developed using a catalytic amount of cerium(IV) ammonium nitrate at room temperature to afford the corresponding -keto enol ethers in good to excellent yields. The deprotections of enol ethers in water-acetonitrile (1:1) using a catalytic amount (10 mol %) of cerium(IV) ammonium nitrate have also been achieved.

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Mild acetalisation of mono and dicarbonyl compounds catalysed by titanium tetrachloride. Facile synthesis of β-keto enol ethers

Cited by 86 publications

References 29 publications

Facile Reduction of Aromatic Aldehydes, Ketones, Diketones and Oxo Aldehydes to Alcohols by an Aqueous TiCl3/NH3 System: Selectivity and Scope

Facile Reduction of Aromatic Aldehydes, Ketones, Diketones and Oxo Aldehydes to Alcohols by an Aqueous TiCl3/NH3 System: Selectivity and Scope

Design, Synthesis and Biological Evaluation of 3-(4-Halophenyl)-3-oxopropanal and Their Derivatives as Novel Antibacterial Agents

Cerium(IV) Ammonium Nitrate-catalyzed Synthesis of β-Keto Enol Ethers from Cyclic β-Diketones and Their Deprotection

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