Aminopyrazoles are important heterocycles in biologically active molecules.  Reactions of aminopyrazoles, in particular 3-amino-5-aryl(or alkyl)-1H-pyrazoles, are challenging due to the presence of three nucleophilic nitrogens within the molecular framework.  The current work is a study of the selectivity of nucleophilic aromatic substitution (SNAr) of 3-amino-5-aryl-1H-pyrazoles.  The varying degree of hydrogen bonding capability with the pyrazole ring nitrogens and the reaction solvent choice impacts the preference for reaction at the exocyclic amino group or at one of the endocyclic nitrogen reactive site.  Reactions conditions, electrophiles, and product selectivity will be presented.

Investigating the S<sub>N</sub>Ar selectivity of 3-amino-5-aryl-1?H?-pyrazoles

248th National Meeting (2014)

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Investigating the SNAr selectivity of 3-amino-5-aryl-1?H?-pyrazoles

Investigating the S_NAr selectivity of 3-amino-5-aryl-1?H?-pyrazoles