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Molecules 2014, 19(1), 55-66; doi:10.3390/molecules19010055

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

1,* , 2
1 Departamento de Ciencias Básicas, Universidad Autónoma Metropolitana-Azcapotzalco, Avenida San Pablo No. 180, C.P. 02200, México D.F., Mexico 2 Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. San Rafael Atlixco No. 186, C.P. 09340, México D.F., Mexico 3 Departamento de Química, CINVESTAV-IPN, Apdo. Postal 14-740, 07000, México D.F., Mexico
* Author to whom correspondence should be addressed.
Received: 30 October 2013 / Revised: 16 December 2013 / Accepted: 16 December 2013 / Published: 20 December 2013
(This article belongs to the Section Organic Synthesis)
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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.
Keywords: click chemistry; aniline; dibenzylated triazoles; catalysis click chemistry; aniline; dibenzylated triazoles; catalysis
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Mendoza-Espinosa, D.; Negron-Silva, G.E.; Lomas-Romero, L.; Gutierrez-Carrillo, A.; Santillán, R. Pseudo-Four Component Synthesis of Mono- and Di-Benzylated-1,2,3-Triazoles Derived from Aniline. Molecules 2014, 19, 55-66.

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