Synthesis, application and scope of a new protected hydrazine reagent

Article abstract of DOI:10.1016/S0040-4039(97)10634-7

A novel triprotected hydrazine reagen, 1,2-Boc₂-2-Z-hydrazine (3), has been made and investigated with respect to stepwise alkylation/acylation and intermediary deprotection in order to prepare multisubstituted hydrazine derivatives. Alkylation of 3 requires particularly mild basic conditions. Regiospecific cleavage of one Boc-group with acid in monoalkylated product 4 is difficult but can be accomplished with catalytic amounts of Mg(ClO₄)₂ in MeCN at 50°C in 15 min, furnishing 5 which can easily be alkylated to 6. This product has recently been converted to fully substituted derivatives?.