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

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

1
,
1,* , 2
,
2
 and
3
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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Abstract

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 (CC BY 3.0).
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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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