
%0 Journal Article
%A Liepa, Andris J. 
%A Jones, Dionne A. 
%A McCarthy, Thomas D. 
%A Nearn, Roland H. 
%T A Synthesis of 1-Hydroxy-5-(2-substituted aryl)tetrazoles by Directed Lithiation
%J Australian Journal of Chemistry
%D 2000/10/27
%V 53
%N 7
%P 619-622
%K 1-Hydroxy-5-aryltetrazoles; lithiation; alkylation; ortho-substituent.
%R https://doi.org/10.1071/CH00073
%U https://www.publish.csiro.au/paper/CH00073 
%X Dilithiation of 1-hydroxy-5-aryltetrazoles with 2 equiv. of butyllithium in the presence of N,N,N&acute;N&acute;-tetra-methylethylenediamine enables the introduction of ortho-substituents into the aryl ring to form compounds (6a&#8211;e). The hydroxy group of 1-hydroxy-5-phenyltetrazole may be masked by alkylation with 9-anthrylmethyl chloride. The masking group is removed with 1,4-diazabicyclo&#91;2.2.2&#93;octane or migrated to N 3 by treatment with trifluoro-acetic acid to form the N-oxide (10). 
