Bromo-Directed N-2 Alkylation of NH-1,2,3-Triazoles: Efficient Synthesis of Poly-Substituted 1,2,3-Triazoles
Organic Letters2009Vol. 11(23), pp. 5490–5493
Citations Over TimeTop 17% of 2009 papers
Xiao‐jun Wang, Kanwar Sidhu, Li Zhang, Scot Campbell, Nizar Haddad, Diana C. Reeves, Dhileepkumar Krishnamurthy, Chris H. Senanayake
Abstract
Reaction of 4-bromo-NH-1,2,3-triazoles 2 with alkyl halides in the presence of K(2)CO(3) in DMF produced the corresponding 2-substituted 4-bromo-1,2,3-triazoles 5 in a regioselective process. Subsequent Suzuki cross-coupling reaction of these bromides provided an efficient synthesis of 2,4,5-trisubstituted triazoles 3. In addition, reduction of the bromotriazoles by hydrogenation furnished an efficient synthesis of 2,4-disubstituted triazoles 8.
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