Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method
The synthesis and structural diversification of <i>N</i>-heterocycles systems have attracted much attention because of their potential applications. Three 6-aryl-3-methyl-1-phenyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine-5-carbaldehyde <b>4</b> derivat...
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| Format: | Article |
| Language: | English |
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MDPI AG
2022-02-01
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| Series: | Molbank |
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| Online Access: | https://www.mdpi.com/1422-8599/2022/1/M1341 |
| _version_ | 1797444480227344384 |
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| author | Jorge Trilleras Jairo Quiroga Angelina Hormaza |
| author_facet | Jorge Trilleras Jairo Quiroga Angelina Hormaza |
| author_sort | Jorge Trilleras |
| collection | DOAJ |
| description | The synthesis and structural diversification of <i>N</i>-heterocycles systems have attracted much attention because of their potential applications. Three 6-aryl-3-methyl-1-phenyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine-5-carbaldehyde <b>4</b> derivatives, in reaction with acetophenones <b>5</b>, via conventional Claisen–Schmidt condensation reactions, generated the respective enones. The enones were used as electron-deficient olefins in a “<i>formal</i>” [2+3] cycloaddition reaction using <i>p</i>-tosylmethyl isocyanide—TosMIC <b>7</b>. This protocol allows access to 3-(substituted aroyl)-4-heteroaryl pyrrole derivatives by the Van Leusen method. |
| first_indexed | 2024-03-09T13:12:10Z |
| format | Article |
| id | doaj.art-019e1f92181c4b13aa9c73900f8943f5 |
| institution | Directory Open Access Journal |
| issn | 1422-8599 |
| language | English |
| last_indexed | 2024-03-09T13:12:10Z |
| publishDate | 2022-02-01 |
| publisher | MDPI AG |
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| series | Molbank |
| spelling | doaj.art-019e1f92181c4b13aa9c73900f8943f52023-11-30T21:39:41ZengMDPI AGMolbank1422-85992022-02-0120221M134110.3390/M1341Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen MethodJorge Trilleras0Jairo Quiroga1Angelina Hormaza2Grupo de Investigación en Compuestos Heterocíclicos, Universidad del Atlántico, Puerto Colombia 08007, ColombiaGrupo de Investigación de Compuestos Heterocíclicos, Universidad del Valle, Cali 760032, ColombiaGrupo de Investigación en Síntesis, Reactividad y Transformación de Compuestos Orgánicos, Universidad Nacional de Colombia, Medellín 050022, ColombiaThe synthesis and structural diversification of <i>N</i>-heterocycles systems have attracted much attention because of their potential applications. Three 6-aryl-3-methyl-1-phenyl-1<i>H</i>-pyrazolo[3,4-<i>b</i>]pyridine-5-carbaldehyde <b>4</b> derivatives, in reaction with acetophenones <b>5</b>, via conventional Claisen–Schmidt condensation reactions, generated the respective enones. The enones were used as electron-deficient olefins in a “<i>formal</i>” [2+3] cycloaddition reaction using <i>p</i>-tosylmethyl isocyanide—TosMIC <b>7</b>. This protocol allows access to 3-(substituted aroyl)-4-heteroaryl pyrrole derivatives by the Van Leusen method.https://www.mdpi.com/1422-8599/2022/1/M13413,4-substituted pyrrole synthesisTosMICVan Leusen reaction |
| spellingShingle | Jorge Trilleras Jairo Quiroga Angelina Hormaza Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method Molbank 3,4-substituted pyrrole synthesis TosMIC Van Leusen reaction |
| title | Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method |
| title_full | Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method |
| title_fullStr | Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method |
| title_full_unstemmed | Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method |
| title_short | Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method |
| title_sort | synthesis of 3 aroyl 4 heteroarylpyrrole derivatives by the van leusen method |
| topic | 3,4-substituted pyrrole synthesis TosMIC Van Leusen reaction |
| url | https://www.mdpi.com/1422-8599/2022/1/M1341 |
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