SYNTHESIS, APPLICATION AND SCOPE OF A NEW PROTECTED HYDRAZINE REAGENT

A novel triprotected hydrazine reagent, 1,2-Boc(2)-2-Z-hydrazine (3), has been made and investigated with respect to stepwise alkylation/acy lation and intermediary deprotection in order to prepare multisubstitu ted 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 on be accomplished with cata lytic amounts of Mg(ClO4)(2) in MeCN at 50 degrees C in 15 min, furnis hing 5 which can easily be alkylated to 6. This product has recently b een converted to fully substituted derivatives 7. (C) 1998 Elsevier Sc ience Ltd. All lights reserved.