Oxidized multiwalled nanotubes as efficient carbocatalyst for the general synthesis of azines

Abstract

The carbocatalytic synthesis of azines (N-N linked diimines) by mild-oxidized multiwalled carbon nanotubes catalyst (oxMWNT) is presented. The material, just with a 5 %wt. loading, is able to carry out a smooth room-temperature metal-free condensation of aldehydes and hydrazine, without external additives, to obtain a wide library of symmetric and also asymmetric azines in excellent yields, even in gram scale, with an excellent selectivity for aromatic substrates. This methodology allows the synthesis of azines with application in nonlinear optics, and the organic materials and biological active compounds crafting. oxMWNT catalysed the reaction in just 3 h with full recyclability upon the recovery of the catalyst. In addition, due to the inherent oxMWNT oxidative capacity in the presence of nitric acid, we have also developed the one-pot synthesis of azines starting from alcohols.