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Bromo-directed N-2 alkylation of NH-1,2,3-triazoles: efficient synthesis of poly-substituted 1,2,3-triazoles. | LitMetric

Bromo-directed N-2 alkylation of NH-1,2,3-triazoles: efficient synthesis of poly-substituted 1,2,3-triazoles.

Org Lett

Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., Ridgefield, Connecticut 06877, USA.

Published: December 2009

AI Article Synopsis

  • The reaction of 4-bromo-NH-1,2,3-triazoles with alkyl halides in the presence of K(2)CO(3) and DMF yields regioselective 2-substituted triazoles.
  • Subsequent Suzuki cross-coupling of these bromides leads to the efficient production of 2,4,5-trisubstituted triazoles.
  • Additionally, hydrogenation of the bromotriazoles provides a straightforward method for synthesizing 2,4-disubstituted triazoles.

Article 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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Source
http://dx.doi.org/10.1021/ol902334xDOI Listing

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