One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives
The nucleophilic substitution of benzylic bromides with sodium azide was combined with a subsequent copper-catalyzed (3 + 2) cycloaddition with terminal alkynes. This one-pot process was developed with a simple model alkyne, but then applied to more complex alkynes bearing enantiopure 1,2-oxazinyl s...
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| Format: | Article |
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Beilstein-Institut
2023-09-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.19.101 |
| _version_ | 1797668586469195776 |
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| author | Hans-Ulrich Reissig Fei Yu |
| author_facet | Hans-Ulrich Reissig Fei Yu |
| author_sort | Hans-Ulrich Reissig |
| collection | DOAJ |
| description | The nucleophilic substitution of benzylic bromides with sodium azide was combined with a subsequent copper-catalyzed (3 + 2) cycloaddition with terminal alkynes. This one-pot process was developed with a simple model alkyne, but then applied to more complex alkynes bearing enantiopure 1,2-oxazinyl substituents. Hence, the precursor compounds 1,2-, 1,3- or 1,4-bis(bromomethyl)benzene furnished geometrically differing bis(1,2,3-triazole) derivatives. The use of tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) as ligand for the click step turned out to be very advantageous. The compounds with 1,2-oxazinyl end groups can potentially serve as precursors of divalent carbohydrate mimetics, but the reductive cleavage of the 1,2-oxazine rings to aminopyran moieties did not proceed cleanly with these compounds. |
| first_indexed | 2024-03-11T20:31:30Z |
| format | Article |
| id | doaj.art-9f61fd3fd4304ce9b40c8a41e7a38315 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-03-11T20:31:30Z |
| publishDate | 2023-09-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-9f61fd3fd4304ce9b40c8a41e7a383152023-10-02T08:42:12ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972023-09-011911399140710.3762/bjoc.19.1011860-5397-19-101One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivativesHans-Ulrich Reissig0Fei Yu1Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, D-14195 Berlin, Germany Institut für Chemie und Biochemie, Freie Universität Berlin, Takustrasse 3, D-14195 Berlin, Germany The nucleophilic substitution of benzylic bromides with sodium azide was combined with a subsequent copper-catalyzed (3 + 2) cycloaddition with terminal alkynes. This one-pot process was developed with a simple model alkyne, but then applied to more complex alkynes bearing enantiopure 1,2-oxazinyl substituents. Hence, the precursor compounds 1,2-, 1,3- or 1,4-bis(bromomethyl)benzene furnished geometrically differing bis(1,2,3-triazole) derivatives. The use of tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine (TBTA) as ligand for the click step turned out to be very advantageous. The compounds with 1,2-oxazinyl end groups can potentially serve as precursors of divalent carbohydrate mimetics, but the reductive cleavage of the 1,2-oxazine rings to aminopyran moieties did not proceed cleanly with these compounds.https://doi.org/10.3762/bjoc.19.101alkynesazidescopper catalysisnucleophilic substitution1,2-oxazines |
| spellingShingle | Hans-Ulrich Reissig Fei Yu One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives Beilstein Journal of Organic Chemistry alkynes azides copper catalysis nucleophilic substitution 1,2-oxazines |
| title | One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives |
| title_full | One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives |
| title_fullStr | One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives |
| title_full_unstemmed | One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives |
| title_short | One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives |
| title_sort | one pot nucleophilic substitution double click reactions of biazides leading to functionalized bis 1 2 3 triazole derivatives |
| topic | alkynes azides copper catalysis nucleophilic substitution 1,2-oxazines |
| url | https://doi.org/10.3762/bjoc.19.101 |
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