Detrifluoroacetylation Reaction of Trifluoromethyl‐β‐diketones: Facile Method for the Synthesis of Succinimide Derivatives and 1,4‐Diketones

Wang, Lihua; Zhao, Jing

doi:10.1002/ejoc.201800680

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Table 1 Optimization Of the Reaction Conditions For The Synt1

S261

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2019

2024

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Cited by 6 publications

(2 citation statements)

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“…Due to compound 1a suffering elimination of COCF 3 (in the form of trifluoroacetic acid) 29 when the literature conditions were employed, 28 we used solvents other than acetic acid to optimize the reactions conditions. The choice of solvents shown in Table 1 was based on the ability to solubilize 2a.…”

Section: Table 1 Optimization Of the Reaction Conditions For The Syntmentioning

confidence: 99%

Regioselective Synthesis of 5-(Trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidines from β-Enamino Diketones

Andrade¹,

Mittersteiner²,

Bonacorso³

et al. 2019

Synthesis

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The use of β-enamino diketones as an easy entry to the regioselective synthesis of [1,2,4]triazolo[1,5-a]pyrimidines is reported. These ketones reacted with 3-amino-1H-1,2,4-triazoles to furnish exclusively 6-substituted 5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidines in yields of up to 95%. The regioselectivity of the reactions performed was maintained regardless of the substituent in the starting ketone or aminoazole.

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Section: Table 1 Optimization Of the Reaction Conditions For The Syntmentioning

confidence: 99%

Regioselective Synthesis of 5-(Trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidines from β-Enamino Diketones

Andrade¹,

Mittersteiner²,

Bonacorso³

et al. 2019

Synthesis

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“…The spectral data S27 are in accordance with those reported in the literature. [8] 7 Gram-scale synthesis of 3u…”

Section: S26mentioning

confidence: 99%

Stereoselective Synthesis of Silyl Enol Ethers with Acylsilanes and ,-Unsaturated Ketones

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Synthesis of α‐Substituted Succinimides from Glyoxal and Ketene N,S‐Acetals

Zheng

Pan

et al. 2019

Asian J Org Chem

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The reaction of ketene N,S-acetals with glyoxal for the efficient synthesis of α-ketosuccinimides is described. Promoted by concentrated hydrobromide, the reaction proceeded under mild aqueous, metal-free conditions, with broad substrate tolerance. As a result, one CÀ C, one CÀ N, and one CÀ O bond were formed. Mechanistic studies show that this tandem process involves enamine addition, hydrolysis and intramolecular nucleophilic addition. In the proposed mechanism, the amine released as a byproduct plays a promoter role to accelerate the construction of α-ketosuccinimides.[a] Q.

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Detrifluoroacetylation Reaction of Trifluoromethyl‐β‐diketones: Facile Method for the Synthesis of Succinimide Derivatives and 1,4‐Diketones

Cited by 6 publications

References 63 publications

Regioselective Synthesis of 5-(Trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidines from β-Enamino Diketones

Regioselective Synthesis of 5-(Trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidines from β-Enamino Diketones

Stereoselective Synthesis of Silyl Enol Ethers with Acylsilanes and ,-Unsaturated Ketones

Synthesis of α‐Substituted Succinimides from Glyoxal and Ketene N,S‐Acetals

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