Phenylselanyl-1H-1,2,3-triazole-4-carbonitriles: synthesis, antioxidant properties and use as precursors to highly functionalized tetrazoles
We describe herein our results on the synthesis, antioxidant properties and chemical diversification of phenylselanyl-1 H -1,2,3-triazole-4-carbonitriles. These compounds were synthesized in high yields by the reaction of azidophenyl phenylselenides with a range of α-keto nitriles, using DMSO as the...
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| Veröffentlicht in: | RSC advances 2016-01, Vol.6 (10), p.8021-8031 |
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| container_title | RSC advances |
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| creator | Savegnago, Lucielli Sacramento, Manoela do Brod, Lucimar M. P. Fronza, Mariana G. Seus, Natália Lenardão, Eder J. Paixão, Márcio W. Alves, Diego |
| description | We describe herein our results on the synthesis, antioxidant properties and chemical diversification of phenylselanyl-1
H
-1,2,3-triazole-4-carbonitriles. These compounds were synthesized in high yields by the reaction of azidophenyl phenylselenides with a range of α-keto nitriles, using DMSO as the solvent in the presence of a catalytic amount of Et
2
NH (1 mol%). The synthesized compounds were screened for their
in vitro
antioxidant activity and 5-phenyl-1-(2-(phenylselanyl)phenyl)-1
H
-1,2,3-triazole-4-carbonitrile (
3a
) exhibited the highest antioxidant effect. In addition, the obtained triazoyl carbonitriles were readily transformed into more complex products
via
a cycloaddition protocol with NaN
3
, affording bifunctional hybrids containing triazole and tetrazole systems in good to excellent yields. |
| doi_str_mv | 10.1039/c5ra22445d |
| format | Article |
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H
-1,2,3-triazole-4-carbonitriles. These compounds were synthesized in high yields by the reaction of azidophenyl phenylselenides with a range of α-keto nitriles, using DMSO as the solvent in the presence of a catalytic amount of Et
2
NH (1 mol%). The synthesized compounds were screened for their
in vitro
antioxidant activity and 5-phenyl-1-(2-(phenylselanyl)phenyl)-1
H
-1,2,3-triazole-4-carbonitrile (
3a
) exhibited the highest antioxidant effect. In addition, the obtained triazoyl carbonitriles were readily transformed into more complex products
via
a cycloaddition protocol with NaN
3
, affording bifunctional hybrids containing triazole and tetrazole systems in good to excellent yields.</description><identifier>ISSN: 2046-2069</identifier><identifier>EISSN: 2046-2069</identifier><identifier>DOI: 10.1039/c5ra22445d</identifier><language>eng</language><subject>antioxidant activity ; Antioxidants ; Catalysis ; cycloaddition reactions ; dimethyl sulfoxide ; Nitriles ; Precursors ; sodium azide ; Solvents ; Synthesis ; Tetrazoles ; Triazoles</subject><ispartof>RSC advances, 2016-01, Vol.6 (10), p.8021-8031</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c367t-c174f51e9d32cbf4e9b444e658813581643c1a45b6100d60df71b28b81751ee23</citedby><cites>FETCH-LOGICAL-c367t-c174f51e9d32cbf4e9b444e658813581643c1a45b6100d60df71b28b81751ee23</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Savegnago, Lucielli</creatorcontrib><creatorcontrib>Sacramento, Manoela do</creatorcontrib><creatorcontrib>Brod, Lucimar M. P.</creatorcontrib><creatorcontrib>Fronza, Mariana G.</creatorcontrib><creatorcontrib>Seus, Natália</creatorcontrib><creatorcontrib>Lenardão, Eder J.</creatorcontrib><creatorcontrib>Paixão, Márcio W.</creatorcontrib><creatorcontrib>Alves, Diego</creatorcontrib><title>Phenylselanyl-1H-1,2,3-triazole-4-carbonitriles: synthesis, antioxidant properties and use as precursors to highly functionalized tetrazoles</title><title>RSC advances</title><description>We describe herein our results on the synthesis, antioxidant properties and chemical diversification of phenylselanyl-1
H
-1,2,3-triazole-4-carbonitriles. These compounds were synthesized in high yields by the reaction of azidophenyl phenylselenides with a range of α-keto nitriles, using DMSO as the solvent in the presence of a catalytic amount of Et
2
NH (1 mol%). The synthesized compounds were screened for their
in vitro
antioxidant activity and 5-phenyl-1-(2-(phenylselanyl)phenyl)-1
H
-1,2,3-triazole-4-carbonitrile (
3a
) exhibited the highest antioxidant effect. In addition, the obtained triazoyl carbonitriles were readily transformed into more complex products
via
a cycloaddition protocol with NaN
3
, affording bifunctional hybrids containing triazole and tetrazole systems in good to excellent yields.</description><subject>antioxidant activity</subject><subject>Antioxidants</subject><subject>Catalysis</subject><subject>cycloaddition reactions</subject><subject>dimethyl sulfoxide</subject><subject>Nitriles</subject><subject>Precursors</subject><subject>sodium azide</subject><subject>Solvents</subject><subject>Synthesis</subject><subject>Tetrazoles</subject><subject>Triazoles</subject><issn>2046-2069</issn><issn>2046-2069</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFUctKxEAQDKKgqBe_YI4iOzrvJN6W9QkLiug5TCYddySbrNMTcPcb_GhH14M3-1JNUd1ddGXZCWfnnMnywulghVBKNzvZgWDKUMFMufun38-OEd9YKqO5MPwg-3xcQL_uEDqbgPI7yidiImkM3m6GDqiizoZ66H1iOsBLgus-LgA9Tojtox8-fJOQrMKwghA9YKIbMiIQi4kFNwYcApI4kIV_XXRr0o69S4O97fwGGhIhhp9beJTttTZ5Of7Fw-zl5vp5dkfnD7f3s-mcOmnySB3PVas5lI0Urm4VlLVSCowuCi51wY2Sjlula8MZawxr2pzXoqgLnqcpEPIwO93uTabfR8BYLT066NIPYBixEkJLyZgq2L9SXgitjcxLmaRnW6kLA2KAtloFv7RhXXFWfQdUzfTT9CegK_kFlHaEag</recordid><startdate>20160101</startdate><enddate>20160101</enddate><creator>Savegnago, Lucielli</creator><creator>Sacramento, Manoela do</creator><creator>Brod, Lucimar M. P.</creator><creator>Fronza, Mariana G.</creator><creator>Seus, Natália</creator><creator>Lenardão, Eder J.</creator><creator>Paixão, Márcio W.</creator><creator>Alves, Diego</creator><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7S9</scope><scope>L.6</scope></search><sort><creationdate>20160101</creationdate><title>Phenylselanyl-1H-1,2,3-triazole-4-carbonitriles: synthesis, antioxidant properties and use as precursors to highly functionalized tetrazoles</title><author>Savegnago, Lucielli ; Sacramento, Manoela do ; Brod, Lucimar M. P. ; Fronza, Mariana G. ; Seus, Natália ; Lenardão, Eder J. ; Paixão, Márcio W. ; Alves, Diego</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c367t-c174f51e9d32cbf4e9b444e658813581643c1a45b6100d60df71b28b81751ee23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>antioxidant activity</topic><topic>Antioxidants</topic><topic>Catalysis</topic><topic>cycloaddition reactions</topic><topic>dimethyl sulfoxide</topic><topic>Nitriles</topic><topic>Precursors</topic><topic>sodium azide</topic><topic>Solvents</topic><topic>Synthesis</topic><topic>Tetrazoles</topic><topic>Triazoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Savegnago, Lucielli</creatorcontrib><creatorcontrib>Sacramento, Manoela do</creatorcontrib><creatorcontrib>Brod, Lucimar M. P.</creatorcontrib><creatorcontrib>Fronza, Mariana G.</creatorcontrib><creatorcontrib>Seus, Natália</creatorcontrib><creatorcontrib>Lenardão, Eder J.</creatorcontrib><creatorcontrib>Paixão, Márcio W.</creatorcontrib><creatorcontrib>Alves, Diego</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>RSC advances</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Savegnago, Lucielli</au><au>Sacramento, Manoela do</au><au>Brod, Lucimar M. P.</au><au>Fronza, Mariana G.</au><au>Seus, Natália</au><au>Lenardão, Eder J.</au><au>Paixão, Márcio W.</au><au>Alves, Diego</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Phenylselanyl-1H-1,2,3-triazole-4-carbonitriles: synthesis, antioxidant properties and use as precursors to highly functionalized tetrazoles</atitle><jtitle>RSC advances</jtitle><date>2016-01-01</date><risdate>2016</risdate><volume>6</volume><issue>10</issue><spage>8021</spage><epage>8031</epage><pages>8021-8031</pages><issn>2046-2069</issn><eissn>2046-2069</eissn><abstract>We describe herein our results on the synthesis, antioxidant properties and chemical diversification of phenylselanyl-1
H
-1,2,3-triazole-4-carbonitriles. These compounds were synthesized in high yields by the reaction of azidophenyl phenylselenides with a range of α-keto nitriles, using DMSO as the solvent in the presence of a catalytic amount of Et
2
NH (1 mol%). The synthesized compounds were screened for their
in vitro
antioxidant activity and 5-phenyl-1-(2-(phenylselanyl)phenyl)-1
H
-1,2,3-triazole-4-carbonitrile (
3a
) exhibited the highest antioxidant effect. In addition, the obtained triazoyl carbonitriles were readily transformed into more complex products
via
a cycloaddition protocol with NaN
3
, affording bifunctional hybrids containing triazole and tetrazole systems in good to excellent yields.</abstract><doi>10.1039/c5ra22445d</doi><tpages>11</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2046-2069 |
| ispartof | RSC advances, 2016-01, Vol.6 (10), p.8021-8031 |
| issn | 2046-2069 2046-2069 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2253300480 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | antioxidant activity Antioxidants Catalysis cycloaddition reactions dimethyl sulfoxide Nitriles Precursors sodium azide Solvents Synthesis Tetrazoles Triazoles |
| title | Phenylselanyl-1H-1,2,3-triazole-4-carbonitriles: synthesis, antioxidant properties and use as precursors to highly functionalized tetrazoles |
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