Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation
We discuss a novel selenium-based reaction mechanism consisting in a selenoxide elimination-triggered enamine hydrolysis. This one-pot model reaction was studied for a set of substrates. Under oxidative conditions, we observed and characterized the formation of primary and secondary amines as elimin...
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| Format: | Article |
| Language: | English |
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MDPI AG
2021-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/26/9/2770 |
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| author | Giovanni Ribaudo Marco Bortoli Erika Oselladore Alberto Ongaro Alessandra Gianoncelli Giuseppe Zagotto Laura Orian |
| author_facet | Giovanni Ribaudo Marco Bortoli Erika Oselladore Alberto Ongaro Alessandra Gianoncelli Giuseppe Zagotto Laura Orian |
| author_sort | Giovanni Ribaudo |
| collection | DOAJ |
| description | We discuss a novel selenium-based reaction mechanism consisting in a selenoxide elimination-triggered enamine hydrolysis. This one-pot model reaction was studied for a set of substrates. Under oxidative conditions, we observed and characterized the formation of primary and secondary amines as elimination products of such compounds, paving the way for a novel strategy to selectively release bioactive molecules. The underlying mechanism was investigated using NMR, mass spectrometry and density functional theory (DFT). |
| first_indexed | 2024-03-10T11:37:21Z |
| format | Article |
| id | doaj.art-3ba2084877f4426f8741a971773b67a5 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T11:37:21Z |
| publishDate | 2021-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-3ba2084877f4426f8741a971773b67a52023-11-21T18:46:52ZengMDPI AGMolecules1420-30492021-05-01269277010.3390/molecules26092770Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical InvestigationGiovanni Ribaudo0Marco Bortoli1Erika Oselladore2Alberto Ongaro3Alessandra Gianoncelli4Giuseppe Zagotto5Laura Orian6Dipartimento di Medicina Molecolare e Traslazionale, Università degli Studi di Brescia, Viale Europa 11, 25123 Brescia, ItalyDipartimento di Scienze Chimiche, Università degli Studi di Padova, Via Marzolo 1, 35131 Padova, ItalyDipartimento di Medicina Molecolare e Traslazionale, Università degli Studi di Brescia, Viale Europa 11, 25123 Brescia, ItalyDipartimento di Medicina Molecolare e Traslazionale, Università degli Studi di Brescia, Viale Europa 11, 25123 Brescia, ItalyDipartimento di Medicina Molecolare e Traslazionale, Università degli Studi di Brescia, Viale Europa 11, 25123 Brescia, ItalyDipartimento di Scienze del Farmaco, Università degli Studi di Padova, Via Marzolo 5, 35131 Padova, ItalyDipartimento di Scienze Chimiche, Università degli Studi di Padova, Via Marzolo 1, 35131 Padova, ItalyWe discuss a novel selenium-based reaction mechanism consisting in a selenoxide elimination-triggered enamine hydrolysis. This one-pot model reaction was studied for a set of substrates. Under oxidative conditions, we observed and characterized the formation of primary and secondary amines as elimination products of such compounds, paving the way for a novel strategy to selectively release bioactive molecules. The underlying mechanism was investigated using NMR, mass spectrometry and density functional theory (DFT).https://www.mdpi.com/1420-3049/26/9/2770selenoxide eliminationone-potimine-enaminereaction mechanismDFT calculationsselenium |
| spellingShingle | Giovanni Ribaudo Marco Bortoli Erika Oselladore Alberto Ongaro Alessandra Gianoncelli Giuseppe Zagotto Laura Orian Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation Molecules selenoxide elimination one-pot imine-enamine reaction mechanism DFT calculations selenium |
| title | Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation |
| title_full | Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation |
| title_fullStr | Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation |
| title_full_unstemmed | Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation |
| title_short | Selenoxide Elimination Triggers Enamine Hydrolysis to Primary and Secondary Amines: A Combined Experimental and Theoretical Investigation |
| title_sort | selenoxide elimination triggers enamine hydrolysis to primary and secondary amines a combined experimental and theoretical investigation |
| topic | selenoxide elimination one-pot imine-enamine reaction mechanism DFT calculations selenium |
| url | https://www.mdpi.com/1420-3049/26/9/2770 |
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