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

Molecules

Daniel Mendoza-Espinosa¹  Guillermo E. Negron-Silva¹  Leticia Lomas-Romero²  Atilano Gutierrez-Carrillo² 

[1] Departamento de Ciencias Básicas, Universidad Autónoma Metropolitana-Azcapotzalco, Avenida San Pablo No. 180, C.P. 02200, México D.F., Mexico; E-Mail:;Departamento de Química, Universidad Autónoma Metropolitana-Iztapalapa, Av. San Rafael Atlixco No. 186, C.P. 09340, México D.F., Mexico; E-Mails:

关键词: click chemistry;    aniline;    dibenzylated triazoles;    catalysis;   

DOI  :  10.3390/molecules19010055

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2013 by the authors; licensee MDPI, Basel, Switzerland.