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

Autor: Daniel Mendoza-Espinosa, Guillermo E. Negron-Silva, Leticia Lomas-Romero, Atilano Gutierrez-Carrillo, Rosa Santillán
Jazyk: angličtina
Rok vydání: 2013
Předmět:
Zdroj: Molecules, Vol 19, Iss 1, Pp 55-66 (2013)
Druh dokumentu: article
ISSN: 1420-3049
DOI: 10.3390/molecules19010055
Popis: 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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