Synthesis of Fused Tetrazole Derivatives via a Tandem Cycloaddition and <i>N</i>-Allylation Reaction and Parallel Synthesis of Fused Tetrazole Amines

A method for the synthesis of novel fused tricyclic tetrazoles from allylic bromides generated by the recently discovered DiazAll reaction has been developed. This new tandem reaction comprises a cycloaddition between a nitrile and (TMS)N<sub>3</sub> followed by an intramolecular <i>N</i>-allylation. The variation of functionalities in the benzene moiety was well-tolerated, and only a moderate difference in yield and degree of purity was noticed. An <i>exo</i>-methylene group in these new compounds permitted further derivatization. Structural resemblance with substances which possess important pharmacological properties motivated the synthesis of a series of ketones and a small library of amines.