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Preparation of 5-Substituted 1<i>H</i>-Tetrazoles from Nitriles in Water

The Journal of Organic Chemistry · 2001 · Vol. 66(24) · pp. 7945–7950
Zachary DemkoK. Barry Sharpless

Abstract

The addition of sodium azide to nitriles to give 1H-tetrazoles is shown to proceed readily in water with zinc salts as catalysts. The scope of the reaction is quite broad; a variety of aromatic nitriles, activated and unactivated alkyl nitriles, substituted vinyl nitriles, thiocyanates, and cyanamides have all been shown to be viable substrates for this reaction.

Synthesis of Tetrazole DerivativesQuinazolinone synthesis and applicationsCatalytic C–H Functionalization MethodsChemistrySodium azideScope (computer science)Organic chemistryAlkylNitrileZincAzideCatalysisSodium salt

MeSH terms

KineticsNitrilesSolventsTetrazolesWaterZincSodium Azide
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References
The chemistry of the carbon-nitrogen double bond
Journal of Molecular Structure · 1972 · 786 citations
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