A Regioselective Synthesis of 2,4-Disubstituted 2<i>H</i>‑1,2,3-Triazoles by Coupling of <i>N</i>‑Tosylhydrazones and Anhydro-Aldose Tosylhydrazones with 4‑Substituted 1<i>H</i>‑1,2,3-Triazoles - Scope and Limitations.

ABSTRACT: In this paper we present the first investigation of the C-N coupling reaction between N-tosylhydrazones including O-peracylated 2,6-anhydro-aldose tosylhydrazones and 1H-1,2,3-triazoles under catalyst-free conditions. This transformation is characterized by relatively mild thermal conditions, high regioselectivity in favor of 2,4-disubstituted 2H-1,2,3-triazoles and broad functional group tolerance as well as applicability in medicinal chemistry due to the absence of transition metal residues. Tosylhydrazones of aldehydes showed better results in terms of yields (20-61%) than those of ketones (13-16%). From the 1,2,3-triazole side the reactions gave very good results in terms of regioselectivity with both electron-withdrawing and electron-donating groups in the

SUBMITTER: Szakacs B 

PROVIDER: S-EPMC12750258 | biostudies-literature | 2025 Dec

REPOSITORIES: biostudies-literature