A general synthetic method for the formation of substituted 5-aminotetrazoles from thioureas: a strategy for diversity amplification.
A general method for the synthesis of 5-aminotetrazoles is outlined using the mercury(II)-promoted attack of azide anion on a thiourea. The reaction proceeds through a guanyl azide intermediate, which undergoes electrocyclization to the tetrazole. The method is high yielding and provides access to mono-, di-, and trisubstituted 5-aminotetrazoles, targets of potential interest for combinatorial library development.
Batey
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RA
Department of Chemistry, Lash Miller Chemical Laboratories, University of Toronto, Toronto, ON, Canada M5S 3H6. rbatey@chem.utoronto.ca
Powell
D A
DA
D018360:Crystallography, X-Ray; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry; D013777:Tetrazoles / Q000138:chemical synthesis*; D013890:Thiourea / Q000737:chemistry*
D010455:Peptides; D013777:Tetrazoles; D013890:Thiourea