Molecules (Dec 2013)

Pseudo-Four Component Synthesis of Mono- and Di-Benzylated-1,2,3-Triazoles Derived from Aniline

  • Daniel Mendoza-Espinosa,
  • Guillermo E. Negron-Silva,
  • Leticia Lomas-Romero,
  • Atilano Gutierrez-Carrillo,
  • Rosa Santillán

DOI
https://doi.org/10.3390/molecules19010055
Journal volume & issue
Vol. 19, no. 1
pp. 55 – 66

Abstract

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The pseudo-four component click synthesis of dibenzylated 1,2,3-triazoles derived from aniline is reported. The cycloaddition of sodium azide to N-(prop-2-ynyl)-benzenamine (I) in the presence of equimolar amounts of p-substituted benzyl derivatives, yields a mixture of mono- and dibenzylated 1,2,3-triazoles. When two equivalents of the benzyl derivative are added to the multicomponent reaction, the selective preparation of the dibenzylated compounds is achieved. The reactivity of the aniline N-H bond in monobenzylated 1,2,3-triazoles was tested by treatment with one equivalent of a p-substituted benzyl chloride at 40 °C, rendering the dibenzylated derivatives quantitatively.

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