Easy access to 3- or 5-heteroarylamino-1,2,4-triazines by S(N)Ar, S(N)H, and palladium-catalyzed N-heteroarylations

Ethel Garnier; Jérôme Audoux; Eric Pasquinet; Franck Suzenet; Didier Poullain; Bruno Lebret; Gérald Guillaumet

doi:10.1021/jo0490898

Easy access to 3- or 5-heteroarylamino-1,2,4-triazines by S(N)Ar, S(N)H, and palladium-catalyzed N-heteroarylations

J Org Chem. 2004 Nov 12;69(23):7809-15. doi: 10.1021/jo0490898.

Authors

Ethel Garnier¹, Jérôme Audoux, Eric Pasquinet, Franck Suzenet, Didier Poullain, Bruno Lebret, Gérald Guillaumet

Affiliation

¹ Institut de Chimie Organique et Analytique (I.C.O.A.), UMR-CNRS 6005, LRC CEA M09, Université d'Orléans, Rue de Chartres, BP 6759, 45067 Orléans Cedex 2, France.

PMID: 15527255
DOI: 10.1021/jo0490898

Abstract

In this paper, N-arylations between two heteroaryl compounds were studied. Conditions were found to generate selectively either 3- or 5-heteroarylamino-1,2,4-triazines by investigating anionic processes (use of bases such as 2,2',6,6'-tetramethylpiperidine/tBuOK/nBuLi) or Pd-catalyzed N-arylations [Pd(OAc)(2), xantphos]. These methods were successfully applied to a wide variety of heteroarylamines and allowed us to pursue our work on fused polynitrogen compounds synthesis.