Three-component cascade reaction of 3-ketonitriles, 2-unsubstituted imidazole -oxides, and aldehydes
A three-component condensation of 2-unsubstituted imidazole N -oxides, 3-ketonitriles, and aldehydes is described. The reaction proceeds via sequential Knoevenagel condensation/Michael addition under mild, catalyst-free conditions with various substrates. Furthermore, the corresponding 2-functionali...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2024-05, Vol.22 (21), p.4297-438 |
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| container_issue | 21 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Uvarova, Ekaterina S Kutasevich, Anton V Lipatov, Egor S Pytskii, Ivan S Raitman, Oleg A Selivantev, Yuriy M Mityanov, Vitaly S |
| description | A three-component condensation of 2-unsubstituted imidazole
N
-oxides, 3-ketonitriles, and aldehydes is described. The reaction proceeds
via
sequential Knoevenagel condensation/Michael addition under mild, catalyst-free conditions with various substrates. Furthermore, the corresponding 2-functionalized imidazole
N
-oxides can be further dehydrated to (
Z
)-2-aroyl-3-(1
H
-imidazol-2-yl)-acrylonitriles, which may also be directly prepared by changing the reaction conditions as a cascade of Knoevenagel condensation/Michael addition/dehydration.
A three-component condensation of imidazole
N
-oxides, 3-ketonitriles and aldehydes was developed. Mechanistic details were revealed using DFT calculations. |
| doi_str_mv | 10.1039/d4ob00353e |
| format | Article |
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N
-oxides, 3-ketonitriles, and aldehydes is described. The reaction proceeds
via
sequential Knoevenagel condensation/Michael addition under mild, catalyst-free conditions with various substrates. Furthermore, the corresponding 2-functionalized imidazole
N
-oxides can be further dehydrated to (
Z
)-2-aroyl-3-(1
H
-imidazol-2-yl)-acrylonitriles, which may also be directly prepared by changing the reaction conditions as a cascade of Knoevenagel condensation/Michael addition/dehydration.
A three-component condensation of imidazole
N
-oxides, 3-ketonitriles and aldehydes was developed. Mechanistic details were revealed using DFT calculations.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d4ob00353e</identifier><ispartof>Organic & biomolecular chemistry, 2024-05, Vol.22 (21), p.4297-438</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></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>Uvarova, Ekaterina S</creatorcontrib><creatorcontrib>Kutasevich, Anton V</creatorcontrib><creatorcontrib>Lipatov, Egor S</creatorcontrib><creatorcontrib>Pytskii, Ivan S</creatorcontrib><creatorcontrib>Raitman, Oleg A</creatorcontrib><creatorcontrib>Selivantev, Yuriy M</creatorcontrib><creatorcontrib>Mityanov, Vitaly S</creatorcontrib><title>Three-component cascade reaction of 3-ketonitriles, 2-unsubstituted imidazole -oxides, and aldehydes</title><title>Organic & biomolecular chemistry</title><description>A three-component condensation of 2-unsubstituted imidazole
N
-oxides, 3-ketonitriles, and aldehydes is described. The reaction proceeds
via
sequential Knoevenagel condensation/Michael addition under mild, catalyst-free conditions with various substrates. Furthermore, the corresponding 2-functionalized imidazole
N
-oxides can be further dehydrated to (
Z
)-2-aroyl-3-(1
H
-imidazol-2-yl)-acrylonitriles, which may also be directly prepared by changing the reaction conditions as a cascade of Knoevenagel condensation/Michael addition/dehydration.
A three-component condensation of imidazole
N
-oxides, 3-ketonitriles and aldehydes was developed. Mechanistic details were revealed using DFT calculations.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFjk0KwjAYRIMoWH827oUcwGjatJauRfEA7kuafKXRNClJCtbTqyC6dDXzmLcYhFYx3caUFTuZ2opSljEYoShO85zQjBXjb0_oFM28v1IaF_k-jZC8NA6ACNt21oAJWHAvuATsgIugrMG2xozcIFijglMa_AYnpDe-r3xQoQ8gsWqV5A-rARN7V_KtcCMx1xKa4YULNKm59rD85BytT8fL4UycF2XnVMvdUP6us3_7E-WCSE4</recordid><startdate>20240529</startdate><enddate>20240529</enddate><creator>Uvarova, Ekaterina S</creator><creator>Kutasevich, Anton V</creator><creator>Lipatov, Egor S</creator><creator>Pytskii, Ivan S</creator><creator>Raitman, Oleg A</creator><creator>Selivantev, Yuriy M</creator><creator>Mityanov, Vitaly S</creator><scope/></search><sort><creationdate>20240529</creationdate><title>Three-component cascade reaction of 3-ketonitriles, 2-unsubstituted imidazole -oxides, and aldehydes</title><author>Uvarova, Ekaterina S ; Kutasevich, Anton V ; Lipatov, Egor S ; Pytskii, Ivan S ; Raitman, Oleg A ; Selivantev, Yuriy M ; Mityanov, Vitaly S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_d4ob00353e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Uvarova, Ekaterina S</creatorcontrib><creatorcontrib>Kutasevich, Anton V</creatorcontrib><creatorcontrib>Lipatov, Egor S</creatorcontrib><creatorcontrib>Pytskii, Ivan S</creatorcontrib><creatorcontrib>Raitman, Oleg A</creatorcontrib><creatorcontrib>Selivantev, Yuriy M</creatorcontrib><creatorcontrib>Mityanov, Vitaly S</creatorcontrib><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Uvarova, Ekaterina S</au><au>Kutasevich, Anton V</au><au>Lipatov, Egor S</au><au>Pytskii, Ivan S</au><au>Raitman, Oleg A</au><au>Selivantev, Yuriy M</au><au>Mityanov, Vitaly S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Three-component cascade reaction of 3-ketonitriles, 2-unsubstituted imidazole -oxides, and aldehydes</atitle><jtitle>Organic & biomolecular chemistry</jtitle><date>2024-05-29</date><risdate>2024</risdate><volume>22</volume><issue>21</issue><spage>4297</spage><epage>438</epage><pages>4297-438</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A three-component condensation of 2-unsubstituted imidazole
N
-oxides, 3-ketonitriles, and aldehydes is described. The reaction proceeds
via
sequential Knoevenagel condensation/Michael addition under mild, catalyst-free conditions with various substrates. Furthermore, the corresponding 2-functionalized imidazole
N
-oxides can be further dehydrated to (
Z
)-2-aroyl-3-(1
H
-imidazol-2-yl)-acrylonitriles, which may also be directly prepared by changing the reaction conditions as a cascade of Knoevenagel condensation/Michael addition/dehydration.
A three-component condensation of imidazole
N
-oxides, 3-ketonitriles and aldehydes was developed. Mechanistic details were revealed using DFT calculations.</abstract><doi>10.1039/d4ob00353e</doi><tpages>12</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2024-05, Vol.22 (21), p.4297-438 |
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| recordid | cdi_rsc_primary_d4ob00353e |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Three-component cascade reaction of 3-ketonitriles, 2-unsubstituted imidazole -oxides, and aldehydes |
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