Design and synthesis of 3,3'-triazolyl biisoquinoline N , N' -dioxides via Hiyama cross-coupling of 4-trimethylsilyl-1,2,3-triazoles.

Autor: Sun S; Chemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, United States., Reep C; Chemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, United States., Zhang C; Chemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, United States., Captain B; Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, Florida 33146-0431, United States., Peverati R; Chemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, United States., Takenaka N; Chemistry Program, Department of Biomedical and Chemical Engineering and Sciences, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901-6975, United States.
Jazyk: angličtina
Zdroj: Tetrahedron letters [Tetrahedron Lett] 2021 Sep 28; Vol. 81. Date of Electronic Publication: 2021 Aug 21.
DOI: 10.1016/j.tetlet.2021.153338
Abstrakt: A new strategy to effectively lock the conformation of substituents at the 3,3'-positions of axial-chiral biisoquinoline N , N' -dioxides was developed based on the strong dipole-dipole interaction between 1,2,3-triazole and pyridine N -oxide rings. The crystal structure and the DFT calculations of 3,3'-bis(1-benzyl-1 H -1,2,3-triazole-4-yl)-1,1'-biisoquinoline N , N' -dioxide ( 3a ) provided strong support for this strategy. Furthermore, we successfully demonstrated that readily available 4-trimethylsilyl-1,2,3-triazoles are viable nucleophiles for Hiyama cross-coupling.
Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
Databáze: MEDLINE
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