Preparation of 5-substituted 1H-tetrazoles from nitriles in water.
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.
Demko
Z P
ZP
Department of Chemistry and The Skaggs Institute of Chemical Biology, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.
Sharpless
K B
KB
D007700:Kinetics; D009570:Nitriles / Q000737:chemistry*; D019810:Sodium Azide / Q000737:chemistry; D012997:Solvents; D013777:Tetrazoles / Q000138:chemical synthesis*; D014867:Water; D015032:Zinc / Q000737:chemistry
D009570:Nitriles; D012997:Solvents; D013777:Tetrazoles; D014867:Water; D019810:Sodium Azide; D015032:Zinc