Synthesis of (arylselanyl)- and (arylsulfenyl)-alkyl-1,2,3-triazolo-1,3,6-triazonines via a copper-catalyzed multicomponent reaction

Aquino, Thalita B.; Nascimento, José Edmilson R.; Dias, Italo Franco Coelho; Hartwig, Daniela; Barcellos, Thiago; Lenardão, Eder J.; Perin, Gelson; Jacob, Raquel G.

doi:10.1016/j.tetlet.2018.01.072

Cited by 17 publications

(8 citation statements)

References 63 publications

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“…First, on reaction with 2‐azidobenzaldehyde 202 , ortho ‐phenylenediamine 201 is transformed into imine A , while copper catalyst interacts with selenium‐containing alkyne to yield alkyne−copper complex B , which reacts with A to afford intermediate C that is further converted into D via a copper(I)‐catalyzed alkyne−azide cycloaddition [195,196] . Afterward, intramolecular Ullmann‐type coupling of D with the amine group gives rise to the 10‐membered cyclic intermediate E , which experiences a reductive elimination to give the title product 200 , and the regeneration of the copper(I) catalyst closing the catalytic cycle [192] …”

Section: Chemistrymentioning

confidence: 99%

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

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Selenium, originally described as a toxin, turns out to be a crucial trace element for life that appears as selenocysteine and its dimer, selenocystine. From the point of view of drug developments, selenium‐containing drugs are isosteres of sulfur and oxygen with the advantage that the presence of the selenium atom confers antioxidant properties and high lipophilicity, which would increase cell membrane permeation leading to better oral bioavailability. In this article, we have focused on the relevant features of the selenium atom, above all, the corresponding synthetic approaches to access a variety of organoselenium molecules along with the proposed reaction mechanisms. The preparation and biological properties of selenosugars, including selenoglycosides, selenonucleosides, selenopeptides, and other selenium‐containing compounds will be treated. We have attempted to condense the most important aspects and interesting examples of the chemistry of selenium into a single article.

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Section: Chemistrymentioning

confidence: 99%

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Sonego,

de Diego,

Szajnman

et al. 2023

Chemistry A European J

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“…In 2018, Aquino et al synthesized (arylselanyl)-alkyl-1,2,3-triazolo-1,3,6-triazonines via CuI-catalyzed MCR of 2-azidobenzaldehyde, 1,2-diaminobenzene, and various arylchalcogenyl alkynes in dioxane at 100 °C. The reaction included a wide variety of arylchalcogenyl alkynes ( Scheme 3 ) [ 53 ].…”

Section: The One-pot Multicomponent Combinatorial Synthesis Of Ose Co...mentioning

confidence: 99%

One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds

et al. 2022

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“…Similar methodology and reaction conditions were further utilized to access (arylsulfenyl)‐ or (arylselanyl)‐alkyl‐triazolo‐1,3,6‐triazonines 172 from 2‐azidobenzaldehyde 6 , o ‐phenylenediamine 170 and various arylchalcogenyl alkynes 171 [56] . Both the propargyl selenides and selanyl alkynes were investigated.…”

Section: Synthesis Of Fused 123‐triazolesmentioning

confidence: 99%

Progress in the Synthesis of Fused 1,2,3‐Triazoles

et al. 2021

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Fused heterocycles display prodigious prominence in diverse field ranging from medicinal chemistry to material science and chemical biology to catalysis. Owing to biological importance, fused 1,2,3‐triazoles have gained much attention and hence, enormous efforts on its synthesis is given by the chemists. Diverse functionalized fused polycyclic 1,2,3‐triazole heterocycles have been designed using Huisgen's thermal intramolecular cycloaddition, copper catalyzed cycloaddition, bimetallic catalytic, greener and other miscellaneous approaches. Novel methodologies that use modified substrates such as ketones, enals, β‐keto esters, olefins, enones, C−H acids etc. in place of alkynes have been developed. Herein, synthetic methodologies to construct fused 1,2,3‐triazoles are briefly discussed.

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Synthesis of (arylselanyl)- and (arylsulfenyl)-alkyl-1,2,3-triazolo-1,3,6-triazonines via a copper-catalyzed multicomponent reaction

Cited by 17 publications

References 63 publications

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

Organoselenium Compounds: Chemistry and Applications in Organic Synthesis

One-Pot Multicomponent Polymerization, Metal-, and Non-Metal-Catalyzed Synthesis of Organoselenium Compounds

Progress in the Synthesis of Fused 1,2,3‐Triazoles

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