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 nitrogen atom. Through treatment of readily accessible geminal diazides with organic hydrazines under mild thermolysis conditions, a broad spectrum of -alkyl- and -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.
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Synthesis of -Substituted 1,2,3-Triazoles.
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Department of Organic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany.
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Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an 710127, P.R. China.
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Department of Chemistry, University of Michigan-Flint, 303 E. Kearsley St., Flint, Michigan 48502, United States.
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