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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.
- Source :
-
Catalysts (2073-4344) . Sep2022, Vol. 12 Issue 9, pN.PAG-N.PAG. 15p. - Publication Year :
- 2022
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 20734344
- Volume :
- 12
- Issue :
- 9
- Database :
- Academic Search Index
- Journal :
- Catalysts (2073-4344)
- Publication Type :
- Academic Journal
- Accession number :
- 159334234
- Full Text :
- https://doi.org/10.3390/catal12091032