Three-component synthesis of novel trifluoromethyl-containing tetrahydropyran derivatives

Zhang, Jun; Zhang, Min; Cao, Weiguo; Song, Liping; Qian, Qun; Tan, Jiwen; Shao, Min

doi:10.1016/j.jfluchem.2009.02.016

Cited by 5 publications

(3 citation statements)

References 28 publications

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“…). [211] The reaction initiates by Michael addition of ethyl 4,4,4-trifluoro-3-oxobutanoate 1 to cinnamaldehyde 315 in presence of L-proline, followed by imine formation and finally intramolecular cyclization. Product yield is affected by electronic and steric effects of the substituents on aniline.…”

Section: Pyran Derivativesmentioning

confidence: 99%

“…employed L‐proline as organocatalyst in the three‐component reaction between ethyl 4,4,4‐trifluoro‐3‐oxobutanoate 1 , substituted anilines 135 and cinnamaldehyde 315 in EtOH at room temperature, leading to the formation of ethyl‐6‐(arylamino)‐2‐hydroxy‐4‐phenyl‐2‐(trifluoromethyl)tetrahydro‐2 H ‐pyran‐3‐carboxylate derivatives 355 as racemic mixtures (Scheme 123). [211] The reaction initiates by Michael addition of ethyl 4,4,4‐trifluoro‐3‐oxobutanoate 1 to cinnamaldehyde 315 in presence of L‐proline, followed by imine formation and finally intramolecular cyclization. Product yield is affected by electronic and steric effects of the substituents on aniline.…”

Section: Trifluoromethyl‐β‐dicarbonyls Based Synthesis Of Heterocyclesmentioning

confidence: 99%

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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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Section: Pyran Derivativesmentioning

confidence: 99%

Section: Trifluoromethyl‐β‐dicarbonyls Based Synthesis Of Heterocyclesmentioning

confidence: 99%

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

Sumran,

Jain,

Kumar

et al. 2024

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…Mohammadi et al 32 Zhang et al 33 developed an L-proline-catalysed reaction of ethyl 4,4,4-trifluoroacetoacetate, cinnamaldehyde and anilines for the preparation of ethyl 6-(arylamino)-2-hydroxy-4-phenyl-2-(trifluoromethyl)-tetrahydro-2H-pyran-3-carboxylate derivatives 43 in good yields (Scheme 14). These workers have proposed that the cinnamaldehyde first reacts with ethyl 4,4,4-trifluoroacetoacetate in the presence of L-proline as an acid/base catalyst via a Michael reaction to form the intermediate 41, which then reacts with aniline to form the imine intermediate 42; thereafter, the carbonyl group is hydrolysed by water to form the nucleophilic oxygen atom intermediate and, finally, intramolecular cyclisation yields the expected products 43 as racemic mixtures.…”

Section: Electrophilic Nature Of Imine In Mcrsmentioning

confidence: 99%