Modular Synthesis of Azines Bearing a Guanidine Core from N-Heterocyclic Carbene (NHC)-Derived Selenoureas and Diazo Reagents.

Autor: Tonis E; Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, 15771, Athens, Greece., Tzouras NV; Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, 15771, Athens, Greece.; Department of Chemistry and Centre of Sustainable Chemistry, Ghent University, Krijgslaan 281, S-3, 9000, Ghent, Belgium., Bracho Pozsoni N; Department of Chemistry and Centre of Sustainable Chemistry, Ghent University, Krijgslaan 281, S-3, 9000, Ghent, Belgium., Saab M; Department of Chemistry and Centre of Sustainable Chemistry, Ghent University, Krijgslaan 281, S-3, 9000, Ghent, Belgium., Bhandary S; Department of Chemistry and Centre of Sustainable Chemistry, Ghent University, Krijgslaan 281, S-3, 9000, Ghent, Belgium., Van Hecke K; Department of Chemistry and Centre of Sustainable Chemistry, Ghent University, Krijgslaan 281, S-3, 9000, Ghent, Belgium., Nelson DJ; WestCHEM Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, G1 1XL, Scotland., Nahra F; Department of Chemistry and Centre of Sustainable Chemistry, Ghent University, Krijgslaan 281, S-3, 9000, Ghent, Belgium.; VITO (Flemish Institute for Technological Research), Boeretang 200, 2400, Mol, Belgium., Nolan SP; Department of Chemistry and Centre of Sustainable Chemistry, Ghent University, Krijgslaan 281, S-3, 9000, Ghent, Belgium., Vougioukalakis GC; Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, 15771, Athens, Greece.
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2024 Sep 19; Vol. 30 (53), pp. e202401816. Date of Electronic Publication: 2024 Sep 03.
DOI: 10.1002/chem.202401816
Abstrakt: N-Heterocyclic carbene (NHC)-derived selenoureas comprise a fundamentally important class of NHC derivatives, with key applications in coordination chemistry and the determination of NHC electronic properties. Considering the broad reactivity of chalcogen-containing compounds, it is surprising to note that the use of NHC-derived selenoureas as organic synthons remains essentially unexplored. The present contribution introduces a novel, straightforward transformation leading to azines bearing a guanidine moiety, through the reaction of a wide range of NHC-derived selenoureas with commercially available diazo compounds, in the presence of triphenylphosphine. This transformation offers a new approach to such products, having biological, materials chemistry, and organic synthesis applications. The guanidine-bearing azines are obtained in excellent yields, with all manipulations taking place in air. A reaction mechanism is proposed, based on both experimental mechanistic findings and density functional theory (DFT) calculations. A one-pot, multicomponent transesterification reaction between selenoureas, α-diazoesters, alcohols, and triphenylphosphine was also developed, providing highly functionalized azines.
(© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH.)
Databáze: MEDLINE
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