Abstract
A facile and highly efficient protocol for synthesis of new 5-substituted-1H-tetrazoles derivatives using copper-doped silica cuprous sulfate (CDSCS) is described. In this method, the cycloaddition reaction of sodium azide with structurally diverse nitriles involving bioactive N-heterocyclic cores exploiting CDSCS in refluxing H2O/i-PrOH (1:1, v/v) furnishes the corresponding 5-substituted-1H-tetrazoles in good to excellent yields (up to 93%). The influence of parameters effective in progress of reaction including solvent type, temperature and catalyst was studied and discussed. In this protocol, CDSCS was proved to be an efficient heterogeneous nano-catalyst to easily achieve the new tetrazole derivatives. The advantages of CDSCS in current protocol known are its cheapness, thermal and chemical stability, ease of recyclability and reusability for several consecutive runs without significant decline in its reactivity.
Highlights
Tetrazole and its derivatives are an important class of N-heterocyclic compounds exhibiting widespread applications.[1,2] Tetrazoles are extensively applied in different industries as instance: stabilizers in photography and photo imaging,[3,4] explosives in rocket propellants,[5,6,7] chelating agents in coordination chemistry,[8,9] plant growth regulators, herbicides, fungicides in agriculture,[3,10] and anti-wears and frictions in lubricants.[11]
To access tetrazoles 2, the cycloaddition reaction of nitriles 1 with sodium azide was carried out utilizing copper-doped silica cuprous sulfate (CDSCS) in H2O/i-PrOH at reflux condition
The reaction of the selected nucleophiles with above chloronitriles was carried out using TEA-K2CO3 (1:1) in the presence of tetrabutylammonium iodide (TBAI) in refluxing MeCN to gain 1
Summary
Tetrazole and its derivatives are an important class of N-heterocyclic compounds exhibiting widespread applications.[1,2] Tetrazoles are extensively applied in different industries as instance: stabilizers in photography and photo imaging,[3,4] explosives in rocket propellants,[5,6,7] chelating agents in coordination chemistry,[8,9] plant growth regulators, herbicides, fungicides in agriculture,[3,10] and anti-wears and frictions in lubricants.[11].
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