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Jazmin Rivers
Chemistry

Mike Haley, Mentor

Metal-mediated cyclization of 2-(Phenylazo)benzonitriles: New methods for the generation of the isoindazole nucleus

Heterocyclic compounds are important in organic synthesis due to their prevalence in biologically active compounds, such as inhibitors and anti-tumor agents. The indazole moiety constitutes the key subunit in many drug substances with a broad range of pharmacological activities. Structurally related isoindazoles, which have only recently begun to be investigated in drug discovery programs, have received only cursory examination due to the many synthetic difficulties of accessing this heterocyclic core. This paper focus on the cyclization of 2-(phenylazo)benzonitriles, which in turn are prepared in 3 steps from commercially available anilines. Depending on the reaction conditions, cyclization of the 2-(phenylazo)benzonitriles with SnCl2 in EtOH gives good yields of 3-aminoisoindazoles, whereas use of ZnCl2 in the presence of excess alkene affords aziridines by way of the isondazolylnitrene.