[tetrazole]Tetrazoles have been a subject of investigation since they were first prepared in the late nineteenth century. They exhibit interesting chemical and biological activity due to their acidic properties which allow them to serve as carboxylic acid bioisosteres. In addition they are not found in nature. Our research has been involved for some time in the preparing of 1 and 2 substituted 5-amino-tetrazoles that could be readily incorporated into commercially interesting products and intermediates. Previously, we found that when one protects the 5-amino group with a benzyl group the favored alkylation product is the 2 position over the 1 position on the heterocycle ring. We have chosen to investigate a boc protecting group's effects on the alkylation in that it can be easily removed via an acid deprotection rather than hdrogenation method used previously.

Control of one vs. two alkylation of 5-amino tetrazoles and the effect of different protecting groups

247th National Meeting (2014)

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