Regioselective synthesis of 2-aryl-5-(polyfluoroalkyl)pyridazin-3-ones based on 2-arylhydrazinylidene 1,3-dicarbonyl compounds

Elkina, Natalia А.; Shchegolkov, Evgeny V.; Burgart, Yanina V.; Perminova, A. N.; Салоутин, В. И.

doi:10.1007/s11172-023-3862-8

Cited by 1 publication

(1 citation statement)

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“…Elkina et al reported that the reaction of polyfluoroalkylcontaining 2-arylhydrazinylidene 1,3-dicarbonyl compounds 144 with ethyl (triphenylphosphoranylidene)acetate 427 in boiling toluene chemo-and regioselectively leads to 3-6carbonyl-functionalized 2-aryl-5-(polyfluoroalkyl)-pyridazin-3ones 428 in 46-77 % yield (Scheme 149). [248] Initial addition of the nucleophilic center of phosphorus ylide 427 A to one of the carbonyl groups of…”

Section: Pyridazine Derivativesmentioning

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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Section: Pyridazine Derivativesmentioning

confidence: 99%