Phenoxydifluoromethyl Substituted Nitrogen Heterocycles. Synthesis and Heterocyclization Reactions of Ethyl 4,4-Difluoro- 4-phenoxyacetoacetate

Sy, Solodukhin; As, Peregudov; ́ev, V.P. Grigor; Nd, Chkanikov

doi:10.3390/90300164

Cited by 3 publications

(2 citation statements)

References 9 publications

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“…We developed a synthetic approach to CF2X-substituted acetoacetic esters: ethyl 4,4-difluoro-4phenoxyacetoacetate and ethyl 4-fluoro-4phenylthioacetoacetate. The new synthons were obtained by the condensation of fluorine-containing acetates with ethyl acetate in the presence of either NaH or lithium diisopropylamide (LDA) (Scheme 21) [53,54]. 2-Trifluoroacetylanilines represent important synthons for the introduction of CF3 groups into different biologically active heterocycles [14,15].…”

Section: Scheme 20mentioning

confidence: 99%

New Approaches to the Synthesis of CF2X-substituted Heterocyclic Antitumor Cytostatic Agents

Чкаников¹,

Golubev²,

Belyaeva³

2019

INEOS OPEN

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This review summarizes recent investigations on the synthesis of fluorine-containing heterocyclic cytostatic agents starting from highly electrophilic unsaturated compounds: CF3or CF2X-containing cyanoethylenes, nitroalkenes, and acetoacetic esters. The possibility of introduction of diethoxyphosphoryl groups along with the fluorine-containing substituents into heterocycles is studied extensively. The examples of directed syntheses of fluorine-containing analogs of natural heterocyclic cytostatic agents are considered. The cytotoxic activities of the resulting compounds against several human cancer cell lines are discussed.

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Section: Scheme 20mentioning

confidence: 99%

New Approaches to the Synthesis of CF2X-substituted Heterocyclic Antitumor Cytostatic Agents

Чкаников¹,

Golubev²,

Belyaeva³

2019

INEOS OPEN

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“…Separately, α,α-difluoroalkyl ethers display a wide range of applications in pharmaceuticals, agrochemicals, and material chemistry. , For example, α,α-difluoroalkyl ethers can enhance metabolic stability and control molecular conformation. , Due to the small rotational barrier around the ArO–CF 2 R bond, difluorinated phenyl ethers can access a wide range of conformers versus the parent alkyl-aryl ethers that preferentially reside in the plane of the arene, and versus trifluoromethyl-aryl ethers that reside orthogonally to the plane of the arene . Interestingly, despite the individual significance of the α,α-difluoroketone and α,α-difluoroalkyl ether components, the hybrid α,α-difluorinated-α-phenoxyketone functional group has rarely been reported, with uses as synthetic intermediates en route to other substructures − or as a specialized resin . The lack of synthetic strategies for accessing α,α-difluorinated-α-phenoxyketones precludes evaluation of the properties of the functional group and also impedes its use in medicinal chemistry and chemical biology.…”

Section: Introductionmentioning

confidence: 99%

Cu(II)-Catalyzed Unsymmetrical Dioxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-phenoxyketones

et al. 2022

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Synthesis of new fluorine-containing pyrazolo[3,4-b]pyridinones as promising drug precursors

et al. 2011

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Methods for the synthesis of 4 R 6,7 dihydro 1H pyrazolo[3,4 b]pyridin 6 ones (R = CF 2 SAr and 4 CFHSAr) were developed. The derivatives with R = CF 2 SAr were ob tained by both heterocyclization of 1 substituted 5 aminopyrazoles with ethyl 4,4 difluoro 3 oxo 4 phenylsulfanylbutanoate and replacement of the Br atom in 4 bromodifluoromethyl 6,7 dihydro 1H pyrazolo[3,4 b]pyridin 6 ones by sodium arenethiolates. The fragment 4 CF HSAr was introduced by replacement of the Cl atom in 4 chlorofluoromethyl 6,7 dihydro 1H pyrazolo[3,4 b]pyridin 6 ones by sodium arenethiolates. Oxidation of 4 CF 2 SPh 6,7 dihydro 1H pyrazolo[3,4 b]pyridin 6 ones gave the corresponding sulfoxides; their structures were con firmed by X ray diffraction data.Key words: pyrazolo[3,4 b]pyridines, fluorine containing 6,7 dihydro 1H pyrazolo[3,4 b] pyridin 6 ones, 1 substituted 5 aminopyrazoles, heterocyclization, fluorine containing ethyl acetoacetates, microwave irradiation, arylsulfanyl(difluoro)methyl group, arylsulfinyl(difluoro) methyl group.The pyrazolo[3,4 b]pyridine framework is a key struc tural fragment of many heterocyclic compounds showing a broad spectrum of biological activity. 1 In the last de cade, some heterocycles of this class have been found to regulate the cardiovascular system 2 and possess antiviral, 3 antitumor, 4 antiinflammatory, 5 antimicrobial, 6 and anti parasitic properties. 7 Fluoroalkyl containing pyrazolo [3,4 b]pyridines are also believed to be candidates for med ications and considered to be potential inhibitors of ade nosine deaminase and inosine 5´ monophosphate dehy drogenase. 8 Primary attention has been given to the syn thesis of CF 3 containing pyrazolo[3,4 b]pyridines 1, 9 while derivatives containing the fragment CF 2 were repre sented by CF 2 H containing pyrazolo[3,4 b]pyridines. 8 At the same time, the structural fragment CF 2 , which is ster ically similar to the CH 2 group, contrasts sharply with the latter in polarity and reactivity. 10

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Phenoxydifluoromethyl Substituted Nitrogen Heterocycles. Synthesis and Heterocyclization Reactions of Ethyl 4,4-Difluoro- 4-phenoxyacetoacetate

Cited by 3 publications

References 9 publications

New Approaches to the Synthesis of CF2X-substituted Heterocyclic Antitumor Cytostatic Agents

New Approaches to the Synthesis of CF2X-substituted Heterocyclic Antitumor Cytostatic Agents

Cu(II)-Catalyzed Unsymmetrical Dioxidation of gem-Difluoroalkenes to Generate α,α-Difluorinated-α-phenoxyketones

Synthesis of new fluorine-containing pyrazolo[3,4-b]pyridinones as promising drug precursors

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