Gold(III) Chloride-Mediated Transformation of Furfural to the <i>trans</i>-<i>N</i>,<i>N</i>-4,5-Diaminocyclopent-2-enones in the Presence of Anilines
We investigated the efficient approach of a series of <i>trans</i>-<i>N</i>,<i>N</i>-4,5-substituted-diaminocyclopent-2-enones (<i>trans</i>-DACPs) from furfural and anilines mediated by Gold(III) chloride (HAuCl<sub>4</sub>). The present p...
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-02-01
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| Series: | Chemistry |
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| Online Access: | https://www.mdpi.com/2624-8549/5/1/29 |
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| author | Marina A. Tzani Ioannis N. Lykakis |
| author_facet | Marina A. Tzani Ioannis N. Lykakis |
| author_sort | Marina A. Tzani |
| collection | DOAJ |
| description | We investigated the efficient approach of a series of <i>trans</i>-<i>N</i>,<i>N</i>-4,5-substituted-diaminocyclopent-2-enones (<i>trans</i>-DACPs) from furfural and anilines mediated by Gold(III) chloride (HAuCl<sub>4</sub>). The present protocol required a low amount of the catalysts, 1.5 mol%, open air conditions, the absence of any additives, and short reaction times. The desired <i>trans</i>-DACPs were isolated in good to high yields. The protocol was also applied to secondary amines, leading to the corresponding 4,5-diamino-cyclopent-2-enones in good yields. To the best of our knowledge, this is the first gold-mediated paradigm as an efficient catalyst for the formation of the cyclopentenones core-bearing C-N bonds under mild reaction conditions. |
| first_indexed | 2024-03-11T06:47:14Z |
| format | Article |
| id | doaj.art-fe5f9c0829f24d96bba3ce63a18b176e |
| institution | Directory Open Access Journal |
| issn | 2624-8549 |
| language | English |
| last_indexed | 2024-03-11T06:47:14Z |
| publishDate | 2023-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Chemistry |
| spelling | doaj.art-fe5f9c0829f24d96bba3ce63a18b176e2023-11-17T10:15:43ZengMDPI AGChemistry2624-85492023-02-015139340510.3390/chemistry5010029Gold(III) Chloride-Mediated Transformation of Furfural to the <i>trans</i>-<i>N</i>,<i>N</i>-4,5-Diaminocyclopent-2-enones in the Presence of AnilinesMarina A. Tzani0Ioannis N. Lykakis1Department of Chemistry, Aristotle University of Thessaloniki, University Campus, 54124 Thessaloniki, GreeceDepartment of Chemistry, Aristotle University of Thessaloniki, University Campus, 54124 Thessaloniki, GreeceWe investigated the efficient approach of a series of <i>trans</i>-<i>N</i>,<i>N</i>-4,5-substituted-diaminocyclopent-2-enones (<i>trans</i>-DACPs) from furfural and anilines mediated by Gold(III) chloride (HAuCl<sub>4</sub>). The present protocol required a low amount of the catalysts, 1.5 mol%, open air conditions, the absence of any additives, and short reaction times. The desired <i>trans</i>-DACPs were isolated in good to high yields. The protocol was also applied to secondary amines, leading to the corresponding 4,5-diamino-cyclopent-2-enones in good yields. To the best of our knowledge, this is the first gold-mediated paradigm as an efficient catalyst for the formation of the cyclopentenones core-bearing C-N bonds under mild reaction conditions.https://www.mdpi.com/2624-8549/5/1/29gold catalysisfurfuralanilinesdiaminocyclopentenonesorganic synthesis |
| spellingShingle | Marina A. Tzani Ioannis N. Lykakis Gold(III) Chloride-Mediated Transformation of Furfural to the <i>trans</i>-<i>N</i>,<i>N</i>-4,5-Diaminocyclopent-2-enones in the Presence of Anilines Chemistry gold catalysis furfural anilines diaminocyclopentenones organic synthesis |
| title | Gold(III) Chloride-Mediated Transformation of Furfural to the <i>trans</i>-<i>N</i>,<i>N</i>-4,5-Diaminocyclopent-2-enones in the Presence of Anilines |
| title_full | Gold(III) Chloride-Mediated Transformation of Furfural to the <i>trans</i>-<i>N</i>,<i>N</i>-4,5-Diaminocyclopent-2-enones in the Presence of Anilines |
| title_fullStr | Gold(III) Chloride-Mediated Transformation of Furfural to the <i>trans</i>-<i>N</i>,<i>N</i>-4,5-Diaminocyclopent-2-enones in the Presence of Anilines |
| title_full_unstemmed | Gold(III) Chloride-Mediated Transformation of Furfural to the <i>trans</i>-<i>N</i>,<i>N</i>-4,5-Diaminocyclopent-2-enones in the Presence of Anilines |
| title_short | Gold(III) Chloride-Mediated Transformation of Furfural to the <i>trans</i>-<i>N</i>,<i>N</i>-4,5-Diaminocyclopent-2-enones in the Presence of Anilines |
| title_sort | gold iii chloride mediated transformation of furfural to the i trans i i n i i n i 4 5 diaminocyclopent 2 enones in the presence of anilines |
| topic | gold catalysis furfural anilines diaminocyclopentenones organic synthesis |
| url | https://www.mdpi.com/2624-8549/5/1/29 |
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