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Abstract
1,2,3-Triazole-4-carbaldehydes are useful synthetic intermediates which may play an important role in the discovery of novel applications of the 1,2,3-triazole moiety. In this work, a one-step multigram scale synthesis of 4-formyl-1-(4-nitrophenyl)-1H-1,2,3-triazole (FNPT) as a preferred reagent for the synthesis of 1-alkyl-4-formyltriazoles is described, making use of the commercially available 3-dimethylaminoacrolein and 4-nitrophenyl azide. Next, the earlier reported reaction of FNPT with alkylamines is further explored, and for hexylamine, the one-pot sequential cycloaddition and Cornforth rearrangement is demonstrated. In addition, a useful protocol for the in situ diazotization of 4-nitroaniline is provided. This facilitated the complete hydrolysis of rearranged 4-iminomethyl-1,2,3-triazoles and allowed for the recycling of 4-nitrophenyl azide.
Highlights
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Imine derivatives have been synthesized as interesting ligands in coordination chemistry [19,20,21]. 1-Substituted 4-formyl-1,2,3-triazoles are commonly prepared via a two-step synthesis involving the copper-catalyzed azide-alkyne cycloaddition reaction with azides and propargyl alcohol [2,9,10,11,12,13,15,16,17,18,22] or acetal-protected propargyl aldehydes [3,5,6,8,23,24], followed by oxidation or hydrolysis, respectively
The first aim of this work was a protocol for the(Scheme metal-free synthesis transformation involves a retro of triazoline
Summary
Publisher’s Note: MDPI stays neutral with regard to jurisdictional claims in published maps and institutional affiliations. 1-Substituted 4-formyl-1,2,3-triazoles are commonly prepared via a two-step synthesis involving the copper-catalyzed azide-alkyne cycloaddition reaction with azides and propargyl alcohol [2,9,10,11,12,13,15,16,17,18,22] or acetal-protected propargyl aldehydes [3,5,6,8,23,24], followed by oxidation or hydrolysis, respectively. The complete hydrolysis of the acetal function on the resulting triazoles was observed at 70 °C without the use
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