Triple-Click Chemistry of Selenium Dihalides: Catalytic Regioselective and Highly Efficient Synthesis of Bis-1,2,3-Triazole Derivatives of 9-Selenabicyclo[3.3.1]nonane
The catalytic regioselective and highly efficient synthesis of bis-1,2,3-triazole derivatives of 9-selenabicyclo[3.3.1]nonane was developed. The 1,3-dipolar cycloaddition reaction of 2,6-diazido-9-selenabicyclo[3.3.1]nonane with a variety of terminal acetylenes catalyzed by a copper acetate/sodium a...
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MDPI AG
2022-09-01
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| author | Vladimir A. Potapov Maxim V. Musalov |
| author_facet | Vladimir A. Potapov Maxim V. Musalov |
| author_sort | Vladimir A. Potapov |
| collection | DOAJ |
| description | The catalytic regioselective and highly efficient synthesis of bis-1,2,3-triazole derivatives of 9-selenabicyclo[3.3.1]nonane was developed. The 1,3-dipolar cycloaddition reaction of 2,6-diazido-9-selenabicyclo[3.3.1]nonane with a variety of terminal acetylenes catalyzed by a copper acetate/sodium ascorbate system proceeded in a regioselective fashion, affording 2,6-bis(4-organyl-1,2,3-triazole)-9-selenabicyclo[3.3.1]nonanes in high yields (93–98%). The reaction of 2,6-diazido-9-selenabicyclo[3.3.1]nonane with dimethyl and diethyl acetylenedicarboxylates was carried out as thermal 1,3-dipolar Huisgen cycloaddition giving the corresponding 4,5-disubstituted 1,2,3-triazole derivatives of 9-selenabicyclo[3.3.1]nonane in high yields. The obtained products are potentially bioactive compounds and first representatives of selenium heterocycles combined with two 1,2,3-triazole moieties. 2.6-Diazido-9-selenabicyclo[3.3.1]nonane was obtained in quantitative yield via the reaction of sodium azide with 2,6-dibromo-9-selenabicyclo[3.3.1]nonane at room temperature. The latter compound was synthesized by stereoselective transannular addition of selenium dibromide to cis, cis-1,5-cyclooctadiene. |
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| issn | 2073-4344 |
| language | English |
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| spelling | doaj.art-4b4d119a475440d4a5fd295a325750b32023-11-23T15:31:15ZengMDPI AGCatalysts2073-43442022-09-01129103210.3390/catal12091032Triple-Click Chemistry of Selenium Dihalides: Catalytic Regioselective and Highly Efficient Synthesis of Bis-1,2,3-Triazole Derivatives of 9-Selenabicyclo[3.3.1]nonaneVladimir A. Potapov0Maxim V. Musalov1A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of the Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, RussiaThe catalytic regioselective and highly efficient synthesis of bis-1,2,3-triazole derivatives of 9-selenabicyclo[3.3.1]nonane was developed. The 1,3-dipolar cycloaddition reaction of 2,6-diazido-9-selenabicyclo[3.3.1]nonane with a variety of terminal acetylenes catalyzed by a copper acetate/sodium ascorbate system proceeded in a regioselective fashion, affording 2,6-bis(4-organyl-1,2,3-triazole)-9-selenabicyclo[3.3.1]nonanes in high yields (93–98%). The reaction of 2,6-diazido-9-selenabicyclo[3.3.1]nonane with dimethyl and diethyl acetylenedicarboxylates was carried out as thermal 1,3-dipolar Huisgen cycloaddition giving the corresponding 4,5-disubstituted 1,2,3-triazole derivatives of 9-selenabicyclo[3.3.1]nonane in high yields. The obtained products are potentially bioactive compounds and first representatives of selenium heterocycles combined with two 1,2,3-triazole moieties. 2.6-Diazido-9-selenabicyclo[3.3.1]nonane was obtained in quantitative yield via the reaction of sodium azide with 2,6-dibromo-9-selenabicyclo[3.3.1]nonane at room temperature. The latter compound was synthesized by stereoselective transannular addition of selenium dibromide to cis, cis-1,5-cyclooctadiene.https://www.mdpi.com/2073-4344/12/9/1032acetylenes1,3-dipolar cycloaddition9-selenabicyclo[3.3.1]nonane derivativescopper-catalyzed reactionsregioselective synthesis |
| spellingShingle | Vladimir A. Potapov Maxim V. Musalov Triple-Click Chemistry of Selenium Dihalides: Catalytic Regioselective and Highly Efficient Synthesis of Bis-1,2,3-Triazole Derivatives of 9-Selenabicyclo[3.3.1]nonane Catalysts acetylenes 1,3-dipolar cycloaddition 9-selenabicyclo[3.3.1]nonane derivatives copper-catalyzed reactions regioselective synthesis |
| title | Triple-Click Chemistry of Selenium Dihalides: Catalytic Regioselective and Highly Efficient Synthesis of Bis-1,2,3-Triazole Derivatives of 9-Selenabicyclo[3.3.1]nonane |
| title_full | Triple-Click Chemistry of Selenium Dihalides: Catalytic Regioselective and Highly Efficient Synthesis of Bis-1,2,3-Triazole Derivatives of 9-Selenabicyclo[3.3.1]nonane |
| title_fullStr | Triple-Click Chemistry of Selenium Dihalides: Catalytic Regioselective and Highly Efficient Synthesis of Bis-1,2,3-Triazole Derivatives of 9-Selenabicyclo[3.3.1]nonane |
| title_full_unstemmed | Triple-Click Chemistry of Selenium Dihalides: Catalytic Regioselective and Highly Efficient Synthesis of Bis-1,2,3-Triazole Derivatives of 9-Selenabicyclo[3.3.1]nonane |
| title_short | Triple-Click Chemistry of Selenium Dihalides: Catalytic Regioselective and Highly Efficient Synthesis of Bis-1,2,3-Triazole Derivatives of 9-Selenabicyclo[3.3.1]nonane |
| title_sort | triple click chemistry of selenium dihalides catalytic regioselective and highly efficient synthesis of bis 1 2 3 triazole derivatives of 9 selenabicyclo 3 3 1 nonane |
| topic | acetylenes 1,3-dipolar cycloaddition 9-selenabicyclo[3.3.1]nonane derivatives copper-catalyzed reactions regioselective synthesis |
| url | https://www.mdpi.com/2073-4344/12/9/1032 |
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