Solvent-Free 1,3-Dipolar Cycloadditions of Nitrones for a More Sustainable Synthesis of Glycomimetics
1,3-Dipolar cycloadditions on nitrone dipoles are key reactions to access five-membered heterocycles, which are useful intermediates in the synthesis of biologically relevant glycomimetics. The good atomic balance and high stereoselectivity characteristic of such reactions make them good candidates...
Saved in:
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2025-06-01
|
| Series: | Reactions |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2624-781X/6/2/36 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1849425487836741632 |
|---|---|
| author | Debora Pratesi Alessio Morano Andrea Goti Francesca Cardona Camilla Matassini |
| author_facet | Debora Pratesi Alessio Morano Andrea Goti Francesca Cardona Camilla Matassini |
| author_sort | Debora Pratesi |
| collection | DOAJ |
| description | 1,3-Dipolar cycloadditions on nitrone dipoles are key reactions to access five-membered heterocycles, which are useful intermediates in the synthesis of biologically relevant glycomimetics. The good atomic balance and high stereoselectivity characteristic of such reactions make them good candidates for the development of green protocols. In the present work, these features were maximized by avoiding the use of organic solvents and considering starting materials derived from biomass. Reactions involving (acyclic and cyclic) carbohydrate-derived nitrones as dipoles and levoglucosenone as dipolarophile were considered. Performing selected 1,3-dipolar cycloadditions in neat conditions showed reduced reaction times, maintaining similar selectivity and yields with respect to the classical protocols. The use of microwave irradiation and orbital shaking were also exploited to increase the sustainability of the synthetic protocols. The collected results highlight the potential of solvent-free 1,3-dipolar cycloadditions in the design of efficient synthetic routes according to green chemistry principles, such as prevention, atom economy, safer solvents and auxiliaries, and use of renewable feedstocks. |
| format | Article |
| id | doaj-art-d8d9edb7c93641fc857fa2cc06e5b97d |
| institution | Kabale University |
| issn | 2624-781X |
| language | English |
| publishDate | 2025-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Reactions |
| spelling | doaj-art-d8d9edb7c93641fc857fa2cc06e5b97d2025-08-20T03:29:44ZengMDPI AGReactions2624-781X2025-06-01623610.3390/reactions6020036Solvent-Free 1,3-Dipolar Cycloadditions of Nitrones for a More Sustainable Synthesis of GlycomimeticsDebora Pratesi0Alessio Morano1Andrea Goti2Francesca Cardona3Camilla Matassini4Dipartimento di Chimica “Ugo Schiff” (DICUS), Università di Firenze, Via della Lastruccia 3-13, I-50019 Sesto Fiorentino, FI, ItalyDipartimento di Chimica “Ugo Schiff” (DICUS), Università di Firenze, Via della Lastruccia 3-13, I-50019 Sesto Fiorentino, FI, ItalyDipartimento di Chimica “Ugo Schiff” (DICUS), Università di Firenze, Via della Lastruccia 3-13, I-50019 Sesto Fiorentino, FI, ItalyDipartimento di Chimica “Ugo Schiff” (DICUS), Università di Firenze, Via della Lastruccia 3-13, I-50019 Sesto Fiorentino, FI, ItalyDipartimento di Chimica “Ugo Schiff” (DICUS), Università di Firenze, Via della Lastruccia 3-13, I-50019 Sesto Fiorentino, FI, Italy1,3-Dipolar cycloadditions on nitrone dipoles are key reactions to access five-membered heterocycles, which are useful intermediates in the synthesis of biologically relevant glycomimetics. The good atomic balance and high stereoselectivity characteristic of such reactions make them good candidates for the development of green protocols. In the present work, these features were maximized by avoiding the use of organic solvents and considering starting materials derived from biomass. Reactions involving (acyclic and cyclic) carbohydrate-derived nitrones as dipoles and levoglucosenone as dipolarophile were considered. Performing selected 1,3-dipolar cycloadditions in neat conditions showed reduced reaction times, maintaining similar selectivity and yields with respect to the classical protocols. The use of microwave irradiation and orbital shaking were also exploited to increase the sustainability of the synthetic protocols. The collected results highlight the potential of solvent-free 1,3-dipolar cycloadditions in the design of efficient synthetic routes according to green chemistry principles, such as prevention, atom economy, safer solvents and auxiliaries, and use of renewable feedstocks.https://www.mdpi.com/2624-781X/6/2/361,3-dipolar cycloadditionsnitronesglycomimeticscarbohydrateslevoglucosenonestereoselective syntheses |
| spellingShingle | Debora Pratesi Alessio Morano Andrea Goti Francesca Cardona Camilla Matassini Solvent-Free 1,3-Dipolar Cycloadditions of Nitrones for a More Sustainable Synthesis of Glycomimetics Reactions 1,3-dipolar cycloadditions nitrones glycomimetics carbohydrates levoglucosenone stereoselective syntheses |
| title | Solvent-Free 1,3-Dipolar Cycloadditions of Nitrones for a More Sustainable Synthesis of Glycomimetics |
| title_full | Solvent-Free 1,3-Dipolar Cycloadditions of Nitrones for a More Sustainable Synthesis of Glycomimetics |
| title_fullStr | Solvent-Free 1,3-Dipolar Cycloadditions of Nitrones for a More Sustainable Synthesis of Glycomimetics |
| title_full_unstemmed | Solvent-Free 1,3-Dipolar Cycloadditions of Nitrones for a More Sustainable Synthesis of Glycomimetics |
| title_short | Solvent-Free 1,3-Dipolar Cycloadditions of Nitrones for a More Sustainable Synthesis of Glycomimetics |
| title_sort | solvent free 1 3 dipolar cycloadditions of nitrones for a more sustainable synthesis of glycomimetics |
| topic | 1,3-dipolar cycloadditions nitrones glycomimetics carbohydrates levoglucosenone stereoselective syntheses |
| url | https://www.mdpi.com/2624-781X/6/2/36 |
| work_keys_str_mv | AT deborapratesi solventfree13dipolarcycloadditionsofnitronesforamoresustainablesynthesisofglycomimetics AT alessiomorano solventfree13dipolarcycloadditionsofnitronesforamoresustainablesynthesisofglycomimetics AT andreagoti solventfree13dipolarcycloadditionsofnitronesforamoresustainablesynthesisofglycomimetics AT francescacardona solventfree13dipolarcycloadditionsofnitronesforamoresustainablesynthesisofglycomimetics AT camillamatassini solventfree13dipolarcycloadditionsofnitronesforamoresustainablesynthesisofglycomimetics |