Direct access to 1-aryl-5-amino-1,2,4-triazoles and [1,2,4]triazolo[1,5-a] pyridines by two new single-step reactions from 1,3,4-thiadiazol-2-amines

Oscar Mammoliti, Evelyne M. Quinton, Kristof T J Loones, Anh Tho Nguyen, Johan Wouters, Guy Van Lommen

Research output: Contribution to journalArticle

Abstract

Two new single-step reactions allowing the construction of two heterocyclic motifs are reported. Both processes involve 5-substituted 1,3,4-thiadiazol-2- amines as starting materials. Reaction with 1-fluoro-2-nitrobenzenes in presence of Hünig's base permitted the convenient synthesis of various 3-substituted 1-aryl-5-amino-1,2,4-triazoles. Reaction with 2-chloro-3- nitropyridines and 2-chloro-5-nitropyridines in similar conditions readily gave access to a number of [1,2,4]triazolo[1,5-a]pyridines. In absence of base, adducts composed by one aromatic unit and two thiadiazole units were formed. This observation and previous work by Anders and co-workers led to the suggestion of plausible mechanisms for these reactions.

Original languageEnglish
Pages (from-to)1669-1680
Number of pages12
JournalTetrahedron
Volume69
Issue number5
DOIs
Publication statusPublished - 4 Feb 2013

    Fingerprint

Keywords

  • Aminotriazole
  • Condensation
  • Dimroth rearrangement
  • Ring formation
  • Single-step synthesis
  • Triazolopyridine

Cite this