Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill
Vibration ball-milling in a zirconia-lined vessel afforded clean and quantitative nucleophilic displacement reactions between 4-methoxybenzylthiolate salts and nucleoside 5′-halides or 5′-tosylates in five to 60 minutes. Under these conditions, commonly-encountered nucleoside cyclisation byproducts...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2017-01-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.13.11 |
| _version_ | 1818612901825478656 |
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| author | Olga Eguaogie Patrick F. Conlon Francesco Ravalico Jamie S. T. Sweet Thomas B. Elder Louis P. Conway Marc E. Lennon David R. W. Hodgson Joseph S. Vyle |
| author_facet | Olga Eguaogie Patrick F. Conlon Francesco Ravalico Jamie S. T. Sweet Thomas B. Elder Louis P. Conway Marc E. Lennon David R. W. Hodgson Joseph S. Vyle |
| author_sort | Olga Eguaogie |
| collection | DOAJ |
| description | Vibration ball-milling in a zirconia-lined vessel afforded clean and quantitative nucleophilic displacement reactions between 4-methoxybenzylthiolate salts and nucleoside 5′-halides or 5′-tosylates in five to 60 minutes. Under these conditions, commonly-encountered nucleoside cyclisation byproducts (especially of purine nucleosides) were not observed. Liquid-assisted grinding of the same 5'-iodide and 5′-tosylate substrates with potassium selenocyanate in the presence of DMF produced the corresponding 5′-selenocyanates in variable yields over the course of between one and eleven hours thereby avoiding the preparation and use of hygroscopic tetrabutylammonium salts. |
| first_indexed | 2024-12-16T15:53:35Z |
| format | Article |
| id | doaj.art-6d3b6b6007ef41de80e4fea654d64978 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T15:53:35Z |
| publishDate | 2017-01-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-6d3b6b6007ef41de80e4fea654d649782022-12-21T22:25:38ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972017-01-01131879210.3762/bjoc.13.111860-5397-13-11Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball millOlga Eguaogie0Patrick F. Conlon1Francesco Ravalico2Jamie S. T. Sweet3Thomas B. Elder4Louis P. Conway5Marc E. Lennon6David R. W. Hodgson7Joseph S. Vyle8School of Chemistry and Chemical Engineering, Queen’s University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UKSchool of Chemistry and Chemical Engineering, Queen’s University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UKSchool of Chemistry and Chemical Engineering, Queen’s University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UKSchool of Chemistry and Chemical Engineering, Queen’s University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UKSchool of Chemistry and Chemical Engineering, Queen’s University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UKDurham University, Department of Chemistry, Lower Mountjoy, Stockton Road, Durham DH1 3LE, UKSchool of Chemistry and Chemical Engineering, Queen’s University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UKDurham University, Department of Chemistry, Lower Mountjoy, Stockton Road, Durham DH1 3LE, UKSchool of Chemistry and Chemical Engineering, Queen’s University Belfast, David Keir Building, Stranmillis Road, Belfast BT9 5AG, UKVibration ball-milling in a zirconia-lined vessel afforded clean and quantitative nucleophilic displacement reactions between 4-methoxybenzylthiolate salts and nucleoside 5′-halides or 5′-tosylates in five to 60 minutes. Under these conditions, commonly-encountered nucleoside cyclisation byproducts (especially of purine nucleosides) were not observed. Liquid-assisted grinding of the same 5'-iodide and 5′-tosylate substrates with potassium selenocyanate in the presence of DMF produced the corresponding 5′-selenocyanates in variable yields over the course of between one and eleven hours thereby avoiding the preparation and use of hygroscopic tetrabutylammonium salts.https://doi.org/10.3762/bjoc.13.11ball millchalcogenmechanochemistrynucleophilic substitutionnucleoside |
| spellingShingle | Olga Eguaogie Patrick F. Conlon Francesco Ravalico Jamie S. T. Sweet Thomas B. Elder Louis P. Conway Marc E. Lennon David R. W. Hodgson Joseph S. Vyle Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill Beilstein Journal of Organic Chemistry ball mill chalcogen mechanochemistry nucleophilic substitution nucleoside |
| title | Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill |
| title_full | Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill |
| title_fullStr | Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill |
| title_full_unstemmed | Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill |
| title_short | Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill |
| title_sort | nucleophilic displacement reactions of 5 derivatised nucleosides in a vibration ball mill |
| topic | ball mill chalcogen mechanochemistry nucleophilic substitution nucleoside |
| url | https://doi.org/10.3762/bjoc.13.11 |
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