Abstract

A new, efficient and convenient method for the synthesis of 5-substituted 1H-tetrazole derivatives with a wide range of substituents in good to excellent yields has been developed. The synthesis was performed by the one-pot three-component [3+2]cycloaddition reaction between aldehyde, hydroxylamine and sodium azide in the presence of Cu/C. The reaction probably proceeds by the in situ formation of nitriles followed by successive [3+2]cycloaddition with sodium azide. A variety of aldehydes were used to obtain the corresponding tetrazoles. The catalyst was recovered by simple filtration and reused at least five times without significant loss of catalytic activity. The use of this method offers additional advantages for the synthesis of 5-substituted 1H-tetrazole derivatives, including the easy availability of starting materials, mild conditions, experimental simplicity and good yields.

Highlights

  • Tetrazoles are a representative class of heterocyclic polyaza compounds, which are extensively investigated due to their broad range of applications

  • In continuation of our studies on the synthesis of heterocycles and the use of heterogeneous catalysts in organic reactions,[44,45,46,47,48,49,50,51,52,53,54,55,56] we describe here a new strategy for the preparation of tetrazole derivatives

  • No product was formed during the reaction in H2O, CH3CN and ethanol (Table 1, entries 1–3). In another attempt to synthesize the tetrazole ring, benzaldehyde, hydroxylamine and NaN3 were used in PEG 200 at 120 °C, which provided the desired tetrazole in very low yield (Table 1, entry 4)

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Summary

Introduction

Tetrazoles are a representative class of heterocyclic polyaza compounds, which are extensively investigated due to their broad range of applications. Tetrazole compounds are used in photography,[14] in specialty explosives[15] and in organocatalysis.[16]

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