1,5‐Diketones Synthesis <i>via</i> Three‐Component Cascade Reaction

Xing, Lijuan; Lü, Tao; Fu, Wei-Li; Lou, Mei‐Mei; Chen, Bin; Wang, Zhi-Shen; Jin, Yang; Li, Dan; Wang, Bin

doi:10.1002/adsc.201500691

Cited by 8 publications

(5 citation statements)

References 33 publications

(15 reference statements)

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“…[3k], First, A isomerizes to the enolate B , which then undergoes intramolecular addition to the acyl group to give intermediate C . [4c] The C–C bond cleavage and isomerization of C affords intermediate D . Finally, D gives product 5 through hydrolysis.…”

Section: Resultsmentioning

confidence: 99%

“…New C–C or C–heteroatom bonds were formed simultaneously through Aldol addition, Mannich addition, Michael addition, substitution or halogenation. Although these novel transformations of compounds 1 and 2 have been reported, the direct detrifluoroacetylative reactions of 1,1,1‐trifluoromethyl‐β‐diketone 3 are rare . Compound 3 can be easily prepared by Claisen reaction with various ketones and trifluoroacetates.…”

Section: Introductionmentioning

confidence: 99%

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

Wang

Zhao

2018

Eur J Org Chem

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Currently, a great deal of research efforts are focused on C–C bond activation for development of novel synthetic methodology. In this paper, a detrifluoroacetylation of trifluoromethyl‐β‐diketones is described, which allows for the synthesis of succinimides and 1,4‐diketones through cascade Michael addition/retro‐Claisen reaction and nucleophilic substitution/retro‐Claisen reaction. The readily available trifluoromethyl‐β‐diketones, wide substrate scope, and mild conditions make this method very practical.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Wang

Zhao

2018

Eur J Org Chem

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“…23). [49] Cai and coworkers [50] developed a method for the preparation of methylene-bridged bis-1,3-dicarbonyl compounds. In their reaction, tetramethylethylenediamine (TMEDA) was used as the methylene source, and cuprous iodide as catalyst under aerobic condition (Eq.…”

Section: Methylene Donorsmentioning

confidence: 99%

Application of N-Alkyl Amines as Versatile Building Blocks in Oxidative Coupling Reactions

Yuan¹,

Xia²,

Chang³

et al. 2021

Chinese Journal of Organic Chemistry

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The oxidative functionalization of N-alkylamines is one of the most direct and versatile strategies for the formation of C-C and C-heteroatom bonds. In recent years, N-alkylamines as multifunctional blocks have made great progress in crossdehydrogenation-coupling (CDC) reactions. The recent progress in the application of N-alkylamines is summarized on the basis of different roles in oxidative coupling reactions.

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“…Trifluoromethyl-β-dicarbonyl compounds act as versatile and imperative synthons in synthetic organic chemistry particularly in regio-and stereoselective synthesis, pharmaceutical chemistry, having various applications in many fields owing to their reactivity, stability, safety, easy handling, low cost, and unique chemical properties as well as convenient access. [44,45] They are also extensively used as metal complexing agents, [46] red emissive materials for OLEDs, [47,48] key precursors for several carbocycles and heterocycles, [49] synthons, [50] or reaction intermediates in α-condensation (Aldol, Knoevenagel, etc.). The use of 1,3-dicarbonyls as Michael donors in Michael reaction with enone afforded Michael adduct by creating a carbon-carbon bond at the acceptor's β-carbon.…”

Section: Introductionmentioning

confidence: 99%

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

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Trifluoromethyl group relishes a privileged position in the realm of medicinal chemistry because its incorporation into organic molecules often enhances the bioactivity by altering pharmacological profile of molecule. Trifluoromethyl‐β‐dicarbonyls have emerged as pivotal building blocks in synthetic organic chemistry due to their facile accessibility, stability and remarkable versatility. Owing to presence of nucleophilic and electrophilic sites, they offer multifunctional sites for the reaction. This review covers a meticulous exploration of their multifaceted role, encompassing an in‐depth analysis of mechanism, extensive scope, limitations and wide‐ranging applications in diverse organic synthesis, covering the literature from the 21st century. This comprehensive review encapsulates the applications of trifluoromethyl‐β‐dicarbonyls and their synthetic equivalents as precursors of complex and diverse heterocyclic scaffolds, fused heterocycles and spirocyclic compounds having medicinal and material importance. Their potent synthetic utility in cyclocondenation reactions with binucleophiles, cycloaddition reactions, C‐C bond formations, asymmetric multicomponent reactions using classical/solvent‐free/catalytic synthesis have been presented. Influence of unsymmetrical trifluoromethyl‐β‐diketones on regioselectivity of transformation is also reviewed. This review will benefit the synthetic and pharmaceutical communities to explore trifluoromethyl‐β‐dicarbonyls as trifluoromethyl building blocks for fabrication of heterocyclic scaffolds having implementation into drug discovery programs in the imminent future.

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1,5‐Diketones Synthesis via Three‐Component Cascade Reaction

Cited by 8 publications

References 33 publications

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

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

Application of N-Alkyl Amines as Versatile Building Blocks in Oxidative Coupling Reactions

Trifluoromethyl‐β‐dicarbonyls as Versatile Synthons in Synthesis of Heterocycles

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