A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling Reactions
The first access to <i>N-1</i>, <i>N-4</i> disubstituted pyrrolo[2,3-<i>d</i>][1,2,3]triazoles is reported. The series were generated using a “one-pot” MCR, leading to a single regioisomer of the attempted heteroaromatic skeleton in good yields. Next, the function...
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MDPI AG
2022-07-01
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| author | Simon Garnier Kévin Brugemann Agnieszka Zak Johnny Vercouillie Marie Potier-Cartereau Mathieu Marchivie Sylvain Routier Frédéric Buron |
| author_facet | Simon Garnier Kévin Brugemann Agnieszka Zak Johnny Vercouillie Marie Potier-Cartereau Mathieu Marchivie Sylvain Routier Frédéric Buron |
| author_sort | Simon Garnier |
| collection | DOAJ |
| description | The first access to <i>N-1</i>, <i>N-4</i> disubstituted pyrrolo[2,3-<i>d</i>][1,2,3]triazoles is reported. The series were generated using a “one-pot” MCR, leading to a single regioisomer of the attempted heteroaromatic skeleton in good yields. Next, the functionalization of <i>C-5</i> and <i>C-6</i> positions was investigated. (Het)aryl groups were introduced at the <i>C-5</i> and <i>C-6</i> positions of the pyrrolo[2,3-<i>d</i>][1,2,3]triazoles using regioselective electrophilic brominations followed by Suzuki–Miyaura cross coupling reactions. Palladium-catalyzed cross-coupling conditions were optimized and a representative library of various boronic acids was employed to establish the scope and limitations of the method. |
| first_indexed | 2024-03-09T13:42:47Z |
| format | Article |
| id | doaj.art-ea7b756973de4a7fa346a185b5e0749e |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-09T13:42:47Z |
| publishDate | 2022-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-ea7b756973de4a7fa346a185b5e0749e2023-11-30T21:05:36ZengMDPI AGCatalysts2073-43442022-07-0112882810.3390/catal12080828A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling ReactionsSimon Garnier0Kévin Brugemann1Agnieszka Zak2Johnny Vercouillie3Marie Potier-Cartereau4Mathieu Marchivie5Sylvain Routier6Frédéric Buron7Institut de Chimie Organique et Analytique, ICOA, Université d’Orleans, CNRS UMR 7311, Rue de Chartres, BP 6759, 45067 Orléans, FranceInstitut de Chimie Organique et Analytique, ICOA, Université d’Orleans, CNRS UMR 7311, Rue de Chartres, BP 6759, 45067 Orléans, FranceInstitut de Chimie Organique et Analytique, ICOA, Université d’Orleans, CNRS UMR 7311, Rue de Chartres, BP 6759, 45067 Orléans, FranceiBrain, INSERM, UMR 1253, Université de Tours, 37032 Tours, FranceNutrition, Croissance et Cancer, N2C, INSERM, UMR 1069, Université de Tours, 37032 Tours, FranceCNRS, Bordeaux INP, ICMCB, UMR 5026, University Bordeaux, 33600 Pessac, FranceInstitut de Chimie Organique et Analytique, ICOA, Université d’Orleans, CNRS UMR 7311, Rue de Chartres, BP 6759, 45067 Orléans, FranceInstitut de Chimie Organique et Analytique, ICOA, Université d’Orleans, CNRS UMR 7311, Rue de Chartres, BP 6759, 45067 Orléans, FranceThe first access to <i>N-1</i>, <i>N-4</i> disubstituted pyrrolo[2,3-<i>d</i>][1,2,3]triazoles is reported. The series were generated using a “one-pot” MCR, leading to a single regioisomer of the attempted heteroaromatic skeleton in good yields. Next, the functionalization of <i>C-5</i> and <i>C-6</i> positions was investigated. (Het)aryl groups were introduced at the <i>C-5</i> and <i>C-6</i> positions of the pyrrolo[2,3-<i>d</i>][1,2,3]triazoles using regioselective electrophilic brominations followed by Suzuki–Miyaura cross coupling reactions. Palladium-catalyzed cross-coupling conditions were optimized and a representative library of various boronic acids was employed to establish the scope and limitations of the method.https://www.mdpi.com/2073-4344/12/8/828pyrrolo[2,3-<i>d</i>][1,2,3]triazolesmulticomponent cyclisationSuzuki–Miyaura reaction |
| spellingShingle | Simon Garnier Kévin Brugemann Agnieszka Zak Johnny Vercouillie Marie Potier-Cartereau Mathieu Marchivie Sylvain Routier Frédéric Buron A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling Reactions Catalysts pyrrolo[2,3-<i>d</i>][1,2,3]triazoles multicomponent cyclisation Suzuki–Miyaura reaction |
| title | A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling Reactions |
| title_full | A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling Reactions |
| title_fullStr | A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling Reactions |
| title_full_unstemmed | A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling Reactions |
| title_short | A Facile One-Pot Synthesis of New Poly Functionalized Pyrrolotriazoles via a Regioselective Multicomponent Cyclisation and Suzuki–Miyaura Coupling Reactions |
| title_sort | facile one pot synthesis of new poly functionalized pyrrolotriazoles via a regioselective multicomponent cyclisation and suzuki miyaura coupling reactions |
| topic | pyrrolo[2,3-<i>d</i>][1,2,3]triazoles multicomponent cyclisation Suzuki–Miyaura reaction |
| url | https://www.mdpi.com/2073-4344/12/8/828 |
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