Synthesis of N 2 -Substituted 1,2,3-Triazoles.

Autor: Kunz KA; Department of Organic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany., Springer BL; Department of Organic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany., Klahn P; Department of Organic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany., Aldemir H; Department of Organic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany., Mohr F; Department of Inorganic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany., Kirsch SF; Department of Organic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany.
Jazyk: angličtina
Zdroj: Organic letters [Org Lett] 2024 Oct 18; Vol. 26 (41), pp. 8816-8820. Date of Electronic Publication: 2024 Oct 08.
DOI: 10.1021/acs.orglett.4c03204
Abstrakt: We present a novel synthetic approach for the synthesis of the 1,2,3-triazole core, with a particular focus on the direct and regioselective synthesis of the synthetically more challenging triazoles having additional substituents at the N 2 nitrogen atom. Through treatment of readily accessible geminal diazides with organic hydrazines under mild thermolysis conditions, a broad spectrum of N 2 -alkyl- and N 2 -aryl-1,2,3-triazoles are easily generated. For example, geminal diazides derived from ketoesters, ketoamides, and ketones were converted under the reaction conditions. The product structures were confirmed via NMR as well as single-crystal structure analysis.
Databáze: MEDLINE