Synthesis of Indole-Based Derivatives Containing Ammonium Salts, Diamines and Aminoureas for Organocatalysis
Indole heterocycles have an established reactivity, and these compounds are H-bond donors via a peculiar non-basic NH. However, the indole core has been scarcely employed in organocatalysis, with only a few examples relevant to electrophilic halogenation reported. To expand the range of potential tr...
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MDPI AG
2025-04-01
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| author | Marcello Casertano Brian G. Kelly Malachi W. Gillick-Healy Paolo Grieco Mauro F. A. Adamo |
| author_facet | Marcello Casertano Brian G. Kelly Malachi W. Gillick-Healy Paolo Grieco Mauro F. A. Adamo |
| author_sort | Marcello Casertano |
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| description | Indole heterocycles have an established reactivity, and these compounds are H-bond donors via a peculiar non-basic NH. However, the indole core has been scarcely employed in organocatalysis, with only a few examples relevant to electrophilic halogenation reported. To expand the range of potential transformations achievable via indole catalysis, we have designed a set of new organic species incorporating an indole core, alongside three privelaged chiral moieties found in many known organocatalysts, namely a quaternary ammonium salt, a diamine and an amino-urea. Herein, we report an optimised synthetic route for the preparation of these potential catalytic species in an enantiomerically pure form. The syntheses are conceived to be modular and therefore will allow each of the three single organic catalysts to be expanded into families without alteration of the synthetic layout, therefore leading to a fast optimisation of new asymmetric procedures. |
| format | Article |
| id | doaj-art-d70701d0fe8b4d9e8e0411b55ca74443 |
| institution | Matheson Library |
| issn | 2673-401X |
| language | English |
| publishDate | 2025-04-01 |
| publisher | MDPI AG |
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| series | Organics |
| spelling | doaj-art-d70701d0fe8b4d9e8e0411b55ca744432025-06-25T14:16:20ZengMDPI AGOrganics2673-401X2025-04-01621510.3390/org6020015Synthesis of Indole-Based Derivatives Containing Ammonium Salts, Diamines and Aminoureas for OrganocatalysisMarcello Casertano0Brian G. Kelly1Malachi W. Gillick-Healy2Paolo Grieco3Mauro F. A. Adamo4Department of Pharmacy, University of Naples Federico II, Via D. Montesano, 49, 80131 Naples, ItalyKelAda Pharmachem Ltd., A1.01., Science Centre South, Belfield, D06 C8P3 Dublin, IrelandKelAda Pharmachem Ltd., A1.01., Science Centre South, Belfield, D06 C8P3 Dublin, IrelandDepartment of Pharmacy, University of Naples Federico II, Via D. Montesano, 49, 80131 Naples, ItalyKelAda Pharmachem Ltd., A1.01., Science Centre South, Belfield, D06 C8P3 Dublin, IrelandIndole heterocycles have an established reactivity, and these compounds are H-bond donors via a peculiar non-basic NH. However, the indole core has been scarcely employed in organocatalysis, with only a few examples relevant to electrophilic halogenation reported. To expand the range of potential transformations achievable via indole catalysis, we have designed a set of new organic species incorporating an indole core, alongside three privelaged chiral moieties found in many known organocatalysts, namely a quaternary ammonium salt, a diamine and an amino-urea. Herein, we report an optimised synthetic route for the preparation of these potential catalytic species in an enantiomerically pure form. The syntheses are conceived to be modular and therefore will allow each of the three single organic catalysts to be expanded into families without alteration of the synthetic layout, therefore leading to a fast optimisation of new asymmetric procedures.https://www.mdpi.com/2673-401X/6/2/15indole catalysisquaternary ammonium saltsorganocatalysis |
| spellingShingle | Marcello Casertano Brian G. Kelly Malachi W. Gillick-Healy Paolo Grieco Mauro F. A. Adamo Synthesis of Indole-Based Derivatives Containing Ammonium Salts, Diamines and Aminoureas for Organocatalysis Organics indole catalysis quaternary ammonium salts organocatalysis |
| title | Synthesis of Indole-Based Derivatives Containing Ammonium Salts, Diamines and Aminoureas for Organocatalysis |
| title_full | Synthesis of Indole-Based Derivatives Containing Ammonium Salts, Diamines and Aminoureas for Organocatalysis |
| title_fullStr | Synthesis of Indole-Based Derivatives Containing Ammonium Salts, Diamines and Aminoureas for Organocatalysis |
| title_full_unstemmed | Synthesis of Indole-Based Derivatives Containing Ammonium Salts, Diamines and Aminoureas for Organocatalysis |
| title_short | Synthesis of Indole-Based Derivatives Containing Ammonium Salts, Diamines and Aminoureas for Organocatalysis |
| title_sort | synthesis of indole based derivatives containing ammonium salts diamines and aminoureas for organocatalysis |
| topic | indole catalysis quaternary ammonium salts organocatalysis |
| url | https://www.mdpi.com/2673-401X/6/2/15 |
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