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

Résultats de recherche: Contribution à un journal/une revueArticleRevue par des pairs

Résumé

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.

langue originaleAnglais
Pages (de - à)1669-1680
Nombre de pages12
journalTetrahedron
Volume69
Numéro de publication5
Les DOIs
Etat de la publicationPublié - 4 févr. 2013

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