Selective Synthesis of Benzimidazoles from <i>o</i>-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles
We investigated the catalytic efficacy of supported gold nanoparticles (AuNPs) towards the selective reaction between <i>o</i>-phenylenediamine and aldehydes that yields 2-substituted benzimidazoles. Among several supported gold nanoparticle platforms, the Au/TiO<sub>2</sub>...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-12-01
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| Series: | Nanomaterials |
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| Online Access: | https://www.mdpi.com/2079-4991/10/12/2405 |
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| author | Marina A. Tzani Catherine Gabriel Ioannis N. Lykakis |
| author_facet | Marina A. Tzani Catherine Gabriel Ioannis N. Lykakis |
| author_sort | Marina A. Tzani |
| collection | DOAJ |
| description | We investigated the catalytic efficacy of supported gold nanoparticles (AuNPs) towards the selective reaction between <i>o</i>-phenylenediamine and aldehydes that yields 2-substituted benzimidazoles. Among several supported gold nanoparticle platforms, the Au/TiO<sub>2</sub> provides a series of 2-aryl and 2-alkyl substituted benzimidazoles at ambient conditions, in the absence of additives and in high yields, using the mixture CHCl<sub>3</sub>:MeOH in ratio 3:1 as the reaction solvent. Among the AuNPs catalysts used herein, the Au/TiO<sub>2</sub> containing small-size nanoparticles is found to be the most active towards the present catalytic methodology. The Au/TiO<sub>2</sub> can be recovered and reused at least five times without a significant loss of its catalytic efficacy. The present catalytic synthetic protocol applies to a broad substrate scope and represents an efficient method for the formation of a C–N bond under mild reaction conditions. Notably, this catalytic methodology provides the regio-isomer of the anthelmintic drug, Thiabendazole, in a lab-scale showing its applicability in the efficient synthesis of such <i>N</i>-heterocyclic molecules at industrial levels. |
| first_indexed | 2024-03-10T14:23:57Z |
| format | Article |
| id | doaj.art-1e4da1257b774cc3a14caef94da76d68 |
| institution | Directory Open Access Journal |
| issn | 2079-4991 |
| language | English |
| last_indexed | 2024-03-10T14:23:57Z |
| publishDate | 2020-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Nanomaterials |
| spelling | doaj.art-1e4da1257b774cc3a14caef94da76d682023-11-20T23:08:24ZengMDPI AGNanomaterials2079-49912020-12-011012240510.3390/nano10122405Selective Synthesis of Benzimidazoles from <i>o</i>-Phenylenediamine and Aldehydes Promoted by Supported Gold NanoparticlesMarina A. Tzani0Catherine Gabriel1Ioannis N. Lykakis2Department of Chemistry, Aristotle University of Thessaloniki, University Campus, 54124 Thessaloniki, GreeceHERACLES Research Center, KEDEK, Laboratory of Environmental Engineering (EnvE-Lab), Department of Chemical Engineering, AUTH, 54124 Thessaloniki, GreeceDepartment of Chemistry, Aristotle University of Thessaloniki, University Campus, 54124 Thessaloniki, GreeceWe investigated the catalytic efficacy of supported gold nanoparticles (AuNPs) towards the selective reaction between <i>o</i>-phenylenediamine and aldehydes that yields 2-substituted benzimidazoles. Among several supported gold nanoparticle platforms, the Au/TiO<sub>2</sub> provides a series of 2-aryl and 2-alkyl substituted benzimidazoles at ambient conditions, in the absence of additives and in high yields, using the mixture CHCl<sub>3</sub>:MeOH in ratio 3:1 as the reaction solvent. Among the AuNPs catalysts used herein, the Au/TiO<sub>2</sub> containing small-size nanoparticles is found to be the most active towards the present catalytic methodology. The Au/TiO<sub>2</sub> can be recovered and reused at least five times without a significant loss of its catalytic efficacy. The present catalytic synthetic protocol applies to a broad substrate scope and represents an efficient method for the formation of a C–N bond under mild reaction conditions. Notably, this catalytic methodology provides the regio-isomer of the anthelmintic drug, Thiabendazole, in a lab-scale showing its applicability in the efficient synthesis of such <i>N</i>-heterocyclic molecules at industrial levels.https://www.mdpi.com/2079-4991/10/12/2405gold nanoparticlesbenzimidazolescyclization reactionheterogeneous catalysis<i>o</i>-phenylenediaminethiabendazole |
| spellingShingle | Marina A. Tzani Catherine Gabriel Ioannis N. Lykakis Selective Synthesis of Benzimidazoles from <i>o</i>-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles Nanomaterials gold nanoparticles benzimidazoles cyclization reaction heterogeneous catalysis <i>o</i>-phenylenediamine thiabendazole |
| title | Selective Synthesis of Benzimidazoles from <i>o</i>-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles |
| title_full | Selective Synthesis of Benzimidazoles from <i>o</i>-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles |
| title_fullStr | Selective Synthesis of Benzimidazoles from <i>o</i>-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles |
| title_full_unstemmed | Selective Synthesis of Benzimidazoles from <i>o</i>-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles |
| title_short | Selective Synthesis of Benzimidazoles from <i>o</i>-Phenylenediamine and Aldehydes Promoted by Supported Gold Nanoparticles |
| title_sort | selective synthesis of benzimidazoles from i o i phenylenediamine and aldehydes promoted by supported gold nanoparticles |
| topic | gold nanoparticles benzimidazoles cyclization reaction heterogeneous catalysis <i>o</i>-phenylenediamine thiabendazole |
| url | https://www.mdpi.com/2079-4991/10/12/2405 |
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