Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations

Simple and efficient methods have been developed to obtain cyanomethylamines and azidomethylamines using reactions of methoxymethylamines with TMSCN and TMSN₃, respectively. In the case of dimethylformamide dimethylacetal, only one MeO group was substituted with CN, and an unexpected direction of the subsequent azidation was found. Adducts of azidomethylamines with DMAD were studied, and the base-catalyzed isomerization of symmetric triazoles into non-symmetric ones was revealed.