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Metal-Free Three-Component Domino Approach to Phosphonylated Triazolines and Triazoles

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posted on 15.01.2016, 00:00 authored by Shakir Ahamad, Ruchir Kant, Kishor Mohanan
An efficient, three-component domino reaction between aldehydes, amines, and the Bestmann–Ohira reagent is reported that enables a general, mild, and straightforward access to 1,4,5-trisubstituted 1,2,3-triazolines and triazoles. The reaction proceeds through a domino-condensation/1,3-dipolar cycloaddition sequence to afford the triazoline derivatives with excellent diastereoselectivity. Moreover, when both amine and aldehyde employed for this reaction are aromatic, a spontaneous oxidation afforded 1,4,5-trisubstituted triazoles in moderate yields.