Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions

Hernández-Reyes, C. Xochitl; Ángeles-Beltrán, Deyanira; Lomas‐Romero, Leticia; González‐Zamora, Eduardo; Gaviño, Rubén; Cárdenas, Jorge; Morales‐Serna, José Antonio; Negrón‐Silva, Guillermo E.

doi:10.3390/molecules17033359

Cited by 9 publications

(4 citation statements)

References 39 publications

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“…Next, the silylation of thymine was obtained in 5 min at room temperature in presence of bistrimethylsilylacetamide BSA. The intermediate was directly engaged in nucleophilic substitution reaction with crotyl bromide, chlorotrimethylsilane and sodium iodide [34]. This reaction is performed under ultrasonic activation to afford after seven hours the desired compound 16 in quantitative yield.…”

Section: Chemistrymentioning

confidence: 99%

Highly convergent synthesis and antiviral activity of (E)-but-2-enyl nucleoside phosphonoamidates

Bessières

Hervin

Roy

et al. 2018

European Journal of Medicinal Chemistry

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Several hitherto unknown (E)-but-2-enyl nucleoside phosphonoamidate analogs (ANPs) were prepared directed with nitrogen reagents by cross-metathesis in water-under ultrasound irradiation. Two diastereoisomers were formally identified by X-ray diffraction. These compounds were evaluated against a large spectrum of DNA and RNA viruses. Among them, the phosphonoamidate thymine analogue 19 emerged as the best prodrug against varicella-zoster virus (VZV) with EC values of 0.33 and 0.39 μM for wild-type and thymidine kinase deficient strains, respectively, and a selectivity index ≥200 μM. This breakthrough approach paves the way for new purine and pyrimidine (E)-but-2-enyl phosphonoamidate analogs.

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Section: Chemistrymentioning

confidence: 99%

Highly convergent synthesis and antiviral activity of (E)-but-2-enyl nucleoside phosphonoamidates

Bessières

Hervin

Roy

et al. 2018

European Journal of Medicinal Chemistry

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“…The use of heterogeneous catalyst as solids (e.g.,silica gel, [29] nanosilica, [30] functionalized mesoporouss ilica, [31][32][33] alumina and/or modifieda lumina, [34][35][36][37] nanoaluminos ilicates, [38][39][40][41][42] montmorillonite-K10 clay, [43] sulfated zirconia, [44,45] annotitanium dioxides, [46] heteropolya cids, [47] polyoxometalatei norganic metal oxygen clusters, [48] Amberlyst-15, [49] nanocrystalline zircosilicate, [50] and iron oxides [51] )h as tried to meet the need for more sustainable protocols that assure good regioselective control,o ften lost to competitive polymerization/isomerization of the epoxides.…”

mentioning

confidence: 99%

Green Regio‐ and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent‐Free Conditions

et al. 2016

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The ring-opening reactions of epoxides with amines were efficiently and regioselectively catalyzed by high-surface-area graphite and graphene oxide under metal-free and solventfree conditions. For epoxides withouta ryl groups, catalytic activity waso bserved only for graphene oxide,a nd hence, the activity must have been due to its acidic groups. For styrene oxide, instead,g raphite and graphene oxide exhibited rather similar catalytic activities, and hence, the activity was mainly due to activation of the electrophilic epoxide by p-stacking interactions with the graphitic p system.T he described aminolysis procedure is green and cheap because the catalyst can be recovered and recycled without loss of efficiency.M oreover, these heterogeneous catalysts exert high stereoselective control in the presence of nonracemic epoxidesa nd provide chiral b-aminoa lcohols with enantiomeric excess values up to 99 %.Epoxider ing-opening reactions are useful methods to provide multifunctionalc ompounds ready to be used as versatile intermediates in total synthesis or as precursors of relevant molecules. As three-membered heterocyclic rings,e poxides are more reactive than ethers owing to ring strain anda re susceptible to attack by ar ange of nucleophiles, including nitrogen (e.g.,a mmonia,a mines, and azides), oxygen (e.g.,w ater,a lcohols, phenols, and acids),a nd sulfur (e.g.,t hiols) containing compounds, and this leads to bifunctional molecules of great industrial value.In particular, epoxy ring-opening reactions with amines are well documented, and with the choice of specific physical parameters (e.g.,h eating, [1,2] microwave, [3][4][5] and ultrasound [5] ), the use of polar reaction media (e.g.,i onic liquids, [6] fluoro alcohols, [7] or water under differentp Hc onditions [8,9] ), or the use of catalysts or activators as homogeneousc atalysts (e.g., Brønsteda cids and bases [6,[9][10][11][12][13][14] ands everalm etal salts and/or complexes [15][16][17][18][19][20][21][22][23][24][25][26][27][28] ), good results have been achieved, although most suffer from poor regioselectivity,h igh temperature, and/ or stoichiometrica mountso ft he catalysta nd the use of excess amounts of reagents.The use of heterogeneous catalyst as solids (e.g.,silica gel, [29] nanosilica, [30] functionalized mesoporouss ilica, [31][32][33] alumina and/or modifieda lumina, [34][35][36][37] nanoaluminos ilicates, [38][39][40][41][42] montmorillonite-K10 clay, [43] sulfated zirconia, [44,45] annotitanium dioxides, [46] heteropolya cids, [47] polyoxometalatei norganic metal oxygen clusters, [48] Amberlyst-15, [49] nanocrystalline zircosilicate, [50] and iron oxides [51] )h as tried to meet the need for more sustainable protocols that assure good regioselective control,o ften lost to competitive polymerization/isomerization of the epoxides.However,ametal-free, highly regioselective procedure is still missing. One of the emerging promises in sustainable chemistry is carbon-based materials, whicha re already used in some important synthetic reactions ...

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“…La zirconia sulfatada es un material que se utiliza comúnmente en la síntesis orgánica como catalizador heterogéneo. 18 Este material se puede reutilizar en varios ciclos de reacción gracias a un proceso de reactivación. En nuestro grupo de trabajo se ha utilizado en la reacción Biginilli, 19 en la protección y desprotección de acilales 20 y en la apertura de epóxidos.…”

Section: Discusión De Resultadosunclassified

“…En nuestro grupo de trabajo se ha utilizado en la reacción Biginilli, 19 en la protección y desprotección de acilales 20 y en la apertura de epóxidos. 22 En el presente trabajo la zirconia sulfatada fue utilizada como catalizador en un proceso que genera derivados [(E)-2-nitroetenil]bencenos, los cuales son importantes subunidades que se encuentran presentes en muchas moléculas biológicamente activas, 23 además son de gran interés en síntesis orgánica por su versatilidad al ser transformados en otros grupos funcionales. 24 Los derivados [(E)-2-nitroetenil]bencenos se obtienen comúnmente con la reacción de Henry, 25…”

Section: Discusión De Resultadosunclassified

Síntesis de derivados [(E)-2-nitroetenil]bencenos en presencia de zirconia sulfatada

Vergara Arenas

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Synthesis of Azanucleosides through Regioselective Ring-Opening of Epoxides Catalyzed by Sulphated Zirconia under Microwave and Solvent-Free Conditions

Cited by 9 publications

References 39 publications

Highly convergent synthesis and antiviral activity of (E)-but-2-enyl nucleoside phosphonoamidates

Highly convergent synthesis and antiviral activity of (E)-but-2-enyl nucleoside phosphonoamidates

Green Regio‐ and Enantioselective Aminolysis Catalyzed by Graphite and Graphene Oxide under Solvent‐Free Conditions

Síntesis de derivados [(E)-2-nitroetenil]bencenos en presencia de zirconia sulfatada

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