Abstract
An efficient procedure for the preparation of 1-substituted-1H-1,2,3,4-tetrazoles via a three-component condensation of triethyl orthoformate, amine, and trimethylsilyl azide using inexpensive and environment-friendly FeCl3 as catalyst under solvent-free conditions has been reported. The reaction generates the corresponding 1-substituted tetrazole in excellent yields.
Highlights
Tetrazoles have received considerable attention because of their wide application [1]
The methods reported for the synthesis of 1-substituted tetrazoles involve acid-catalyzed cycloaddition between hydrazoic acid and isocyanides [5] or trimethylsilylazide [6], cyclization between primary amines with an orthocarboxylic acid ester or ethyl orthoformate and sodium azide in the presence of acetic acid [7], acidic ionic liquid [8], ytterbium triflate [9] and natrolite zeolite [10]
We examined the reaction of trimethylsilyazide using several different catalysts and solvents as well as neat conditions (Table 1)
Summary
Tetrazoles have received considerable attention because of their wide application [1]. The methods reported for the synthesis of 1-substituted tetrazoles involve acid-catalyzed cycloaddition between hydrazoic acid and isocyanides [5] or trimethylsilylazide [6], cyclization between primary amines with an orthocarboxylic acid ester or ethyl orthoformate and sodium azide in the presence of acetic acid [7], acidic ionic liquid [8], ytterbium triflate [9] and natrolite zeolite [10]. Each of these reported methods has at least one or
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