Simple Synthesis of 6‐(Trifluoromethyl)‐2,4,5,6‐tetrahydropyrazolo[3,4‐<i>b</i>]pyran Derivatives by One‐Pot, Three‐Component Reactions

Li, Dongmei; Song, Liping; Li, Xianfu; Xing, Chun‐Hui; Peng, Weimin; Zhu, Shizheng

doi:10.1002/ejoc.200601055

Cited by 24 publications

(1 citation statement)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Furthermore ). [329] Aldehydes bearing electron-donating or electron-withdrawing groups and heterocycles were excellent substrates giving products 633 in 43-84 % yields. ).…”

Section: Other Fused and Bridgehead 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

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.

show abstract

“…Furthermore ). [329] Aldehydes bearing electron-donating or electron-withdrawing groups and heterocycles were excellent substrates giving products 633 in 43-84 % yields. ).…”

Section: Other Fused and Bridgehead 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

Simple Synthesis of 6‐(Trifluoromethyl)‐2,4,5,6‐tetrahydropyrazolo[3,4‐b]pyran Derivatives by One‐Pot, Three‐Component Reactions.

Song

et al. 2007

ChemInform

View full text Add to dashboard Cite

Pyran derivatives R 0340Simple Synthesis of 6-(Trifluoromethyl)-2,4,5,6-tetrahydropyrazolo[3,4-b]pyran Derivatives by One-Pot, Three-Component Reactions. -The condensation of equimolar amounts of aromatic aldehydes bearing electron-donating or electron-withdrawing groups with ketoester (I) and pyrazolone (III) affords the target compounds in moderate to good yields. Perfluorobenzaldehyde and butyraldehyde [cf. (V)] do not react.

show abstract

Chiral Brønsted‐Acid‐Catalyzed Enantioselective Arylation of Ethyl Trifluoroacetoacetate and Ethyl Trifluoropyruvate

Nie¹,

Zhang²,

Wang³

et al. 2009

Eur J Org Chem

View full text Add to dashboard Cite

Keywords: Chiral Brønsted acid / Enantioselective arylation / Asymmetric catalysis / OrganocatalysisChiral phosphoric acid was found to be an effective organocatalysts for the direct enantioselective arylation of ethyl 4,4,4-trifluoroacetoacetate (ETFAA). A series of chiral trifluoromethyl-substituted tertiary alcohols were obtained in moderate to high yields with up to 78 % ee. Several desired products were obtained with excellent optical purities after a sin-

show abstract

Simple Synthesis of 6‐(Trifluoromethyl)‐2,4,5,6‐tetrahydropyrazolo[3,4‐b]pyran Derivatives by One‐Pot, Three‐Component Reactions

Cited by 24 publications

References 20 publications

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

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

Simple Synthesis of 6‐(Trifluoromethyl)‐2,4,5,6‐tetrahydropyrazolo[3,4‐b]pyran Derivatives by One‐Pot, Three‐Component Reactions.

Chiral Brønsted‐Acid‐Catalyzed Enantioselective Arylation of Ethyl Trifluoroacetoacetate and Ethyl Trifluoropyruvate

Contact Info

Product

Resources

About