Synthesis of arylselanyl-1H-1,2,3-triazole-4-carboxylates by organocatalytic cycloaddition of azidophenyl arylselenides with β-keto-esters

Seus, Natália; Gonçalves, Lóren C.C.; Deobald, Anna M.; Savegnago, Lucielli; Alves, Diego; Paixão, Márcio W.

doi:10.1016/j.tet.2012.10.007

Cited by 89 publications

(21 citation statements)

References 87 publications

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“…Based on our previous report on such reaction [33], a mixture of substrates 1a (0.3 mmol) and 2a (0.3 mmol) in DMSO (0.6 mL) was stirred at room temperature in the presence of 1 mol % of Et 2 NH as organocatalyst, providing an excellent yield (98%) of the desired product 3a after 2 h (conditions A, Scheme 2). …”

Section: Resultsmentioning

confidence: 99%

Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

Costa¹,

Seus²,

Roehrs³

et al. 2017

Beilstein J. Org. Chem.

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The use of sonochemistry is described in the organocatalytic enamine-azide [3 + 2] cycloaddition between 1,3-diketones and aryl azidophenyl selenides. These sonochemically promoted reactions were found to be amenable to a range of 1,3-diketones or aryl azidophenyl selenides, providing an efficient access to new ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones in good to excellent yields and short reaction times. In addition, this protocol was extended to β-keto esters, β-keto amides and α-cyano ketones. Selanyltriazoyl carboxylates, carboxamides and carbonitriles were synthesized in high yields at short times of reaction under very mild reaction conditions. 694

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Section: Resultsmentioning

confidence: 99%

Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

Costa¹,

Seus²,

Roehrs³

et al. 2017

Beilstein J. Org. Chem.

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“…In 2012, our research group used the β‐enaminone‐azide cycloaddition reaction in the synthesis of arylselanyl‐1 H ‐1,2,3‐triazole‐4‐carboxylates 49 (Scheme ) …”

Section: Organocatalysismentioning

confidence: 99%

Copper Catalysis and Organocatalysis Showing the Way: Synthesis of Selenium‐Containing Highly Functionalized 1,2,3‐Triazoles

Alves

Goldani

Lenardão

et al. 2017

The Chemical Record

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This article provides a comprehensive overview of reported methods - particularly copper- and organocatalyzed reactions - for the regioselective syntheses of selenium-containing 1,2,3-triazoles systems. These chemical entities are prevalent cores in biologically active compounds and functional materials. In view of their unique properties, substantial efforts have been paid for the design and development of practical approaches for the synthesis of these scaffolds.

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“…This heterocyclic system can be a good candidate in the development of new materials, [19] supramolecular chemistry, [20] design of new supported organocatalysts, biotechnology area [21] and in asymmetric synthesis. [22] There are many attempts to obtain liquid crystal properties based on heterocyclic systems. For example, Majumdar et al have reported cholesterol and oxadiazole-based liquid crystal dimers which were found to possess high thermal stability of TGBC*.…”

Section: Introductionmentioning

confidence: 99%

Non-symmetrical liquid crystal dimers armed with azobenzene and 1,2,3-triazole-cholesterol

et al. 2015

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New non-symmetrical dimers which contain respective side units of azobenzene and 1,2,3-triazole-choloesteral have been synthesised from the reaction between 6-azido-[4-(4-acetylphenylazo)phenoxy]alkane and cholesteryl-4-(prop-2-ynyloxy)benzoate. The results show that the derivatives of 6-bromo[4-(4-acetylphenylazo)phenoxy] alkanes which possess the odd alkyl spacers exhibit dimesomorphism of N and SmA phases whilst the members with even numbers are non-mesogenic. However, the 6-azido-[4-(4-acetylphenylazo)phenoxy]-alkanes show N and SmA phases in a wide temperature range. On heating and cooling the target compounds cholesteryl 4-[(1-(6-(4-(4ʹ-acetylphenylazo)phenoxy)alkyl)-1H-1,2,3-triazol-4-yl)methoxy]benzoate show chiral nematic (oily streak and fanshaped texture) and focal conic texture characteristics of smectic A phases with high thermal stability. Present investigation also reveals the effect of the spacer length upon the phase transition temperature. Intercalated arrangement is favoured by the molecules in the smectic phase. The observation is well established by XRD measurement wherein the actual molecular length is smaller than the theoretical value.

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Synthesis of arylselanyl-1H-1,2,3-triazole-4-carboxylates by organocatalytic cycloaddition of azidophenyl arylselenides with β-keto-esters

Cited by 89 publications

References 87 publications

Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

Ultrasound-promoted organocatalytic enamine–azide [3 + 2] cycloaddition reactions for the synthesis of ((arylselanyl)phenyl-1H-1,2,3-triazol-4-yl)ketones

Copper Catalysis and Organocatalysis Showing the Way: Synthesis of Selenium‐Containing Highly Functionalized 1,2,3‐Triazoles

Non-symmetrical liquid crystal dimers armed with azobenzene and 1,2,3-triazole-cholesterol

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