RSS-Feed abonnieren
DOI: 10.1055/a-1477-4630
Divergent Synthesis of Substituted Amino-1,2,4-triazole Derivatives
This work was supported by the National Key Research and Development Plan of China (No 2016YFD0300709) and the National Natural Science Foundation of China (No. 21402234).
Abstract
A divergent efficient assembly of disubstituted 1,2,4-triazoles was established by cyclization of readily accessible N′-nitro-2-hydrocarbylidene-hydrazinecarboximidamides with moderate to excellent yields under mild reaction conditions. This divergent synthetic strategy was achieved simply by varying the reaction conditions. Under acidic conditions, amino-1,2,4-triazoles were obtained by an intramolecular redox reaction involving the NO2 group. Control experiments and DFT studies revealed that this transformation proceeds via an intramolecular 1,3-hydride transfer pathway leading to HNO2 elimination. Under neutral conditions with water as the solvent, nitroimino-1,2,4-triazoles were obtained by oxidative intramolecular annulation under air.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1477-4630.
- Supporting Information
Publikationsverlauf
Eingereicht: 20. Februar 2021
Angenommen nach Revision: 08. April 2021
Accepted Manuscript online:
08. April 2021
Artikel online veröffentlicht:
03. Mai 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany