AgNO3 catalyzed synthesis of 5-substituted-1H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide

•We report silver nitrate as a highly efficient, one-pot, convenient catalyst.•Nitriles to tetrazole conversion occurred under mild condition with highest purity.•Dimethylformamide was found to be the most suitable solvent for one-pot synthesis.•We established authenticity of this methodology by X-r...

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Veröffentlicht in:Tetrahedron letters 2014-03, Vol.55 (11), p.1879-1882
Hauptverfasser: Mani, Pavnesh, Singh, Ashawani Kumar, Awasthi, Satish Kumar
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Sprache:eng
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Zusammenfassung:•We report silver nitrate as a highly efficient, one-pot, convenient catalyst.•Nitriles to tetrazole conversion occurred under mild condition with highest purity.•Dimethylformamide was found to be the most suitable solvent for one-pot synthesis.•We established authenticity of this methodology by X-ray analysis of compound 2j. An efficient one-pot, convenient catalysis for the synthesis of 5-substituted-1H-tetrazoles is reported. The [3+2] cycloaddition involves various nitriles, sodium azide in refluxing DMF and AgNO3 as catalyst to give corresponding 5-substituted-1H-tetrazoles in good to excellent yields. It is expected that the reaction proceeds via in situ formation of a silver azide species, which participates in coordination of nitrile moiety followed by cycloaddition of azide ion to give tetrazole.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2014.01.117