Divergent Synthesis of Substituted Amino-1,2,4-triazole Derivatives

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.

Key words

1,2,4-triazoles - divergent synthesis - redox chemistry - cyclization - heterocycles

Publikationsverlauf

Eingereicht: 20. Februar 2021

Angenommen nach Revision: 08. April 2021

Accepted Manuscript online:
08. April 2021

Artikel online veröffentlicht:
03. Mai 2021

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