The structures of the hydrogen halide salts of glutaronitrile and related compounds, and their conversion to dihydropyridines

The constitutions of the hydrogen halide salts of glutaronitrile are shown by NMR analysis, to be 2,2-dihalo-6-amino-2,3,4,5-tetrahydropyridinium halids (VIII). A simple procedure for converting these materials to 2-amino-6-halo-3,4-dihydropyridines is described. The latter, which are reasonably stable, represent a new and reactive class of functionally substituted dihydropyridines. Salts derived from several other substituted glutaronitriles have also been examined and proof of their structures is presented.