Bromo-Directed N-2 Alkylation of NH-1,2,3-Triazoles: Efficient Synthesis of Poly-Substituted 1,2,3-Triazoles

Xiao-jun Wang*, Kanwar Sidhu, Li Zhang, Scot Campbell, Nizar Haddad, Diana C. Reeves, Dhileepkumar Krishnamurthy and Chris H. Senanayake

*Department of Chemistry, Lash Miller Laboratories, University of Toronto 80 St. George Street, Toronto ON M5S 3H6, Canada, Email: xiao-jun.wangboehringer-ingelheim.com

X.-j. Wang, K. Sidhu, L. Zhang, S. Campbell, N. Haddad, D. C. Reeves, D. Krishnamurthy, C. H. Senanayake, Org. Lett., 2009, 11, 5460-5493.

DOI: 10.1021/ol902334x

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Abstract

Reaction of 4-bromo-NH-1,2,3-triazoles with alkyl halides in the presence of K₂CO₃ in DMF produced the corresponding 2-substituted 4-bromo-1,2,3-triazoles in a regioselective process. Subsequent Suzuki cross-coupling reaction provided an efficient synthesis of 2,4,5-trisubstituted triazoles, whereas hydrogenation furnished an efficient synthesis of 2,4-disubstituted triazoles.

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Key Words

N-Alkylation, 2H-1,2,3-Triazoles

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ID: J54-Y2009-3510