Hydrazidine, V. Synthese und Reaktionen aromatischer und aliphatischer Hydrazidine und deren N 1 ‐substituierter Derivate

Hydrazidines, V. — Synthesis and Reactions of Aromatic and Aliphatic Hydrazidines and Their N 1 ‐Substituted Derivatives Aromatic hydrazidines 3 have been synthetized by reaction of aromatic orthocarboxylates 4 with tert ‐butyl carbazate ( 5 ) and reaction of the protected hydrazidines 7 with HCl/methanol or HBr/acetic acid. Aliphatic N 1 ‐methylhydrazidines 8 have been prepared by methylation of bis ( tert ‐butoxycarbonyl)‐hydrazidines 7 and deprotection with HBr/acetic acid. Aromatic N 1 ‐methylhydrazidines 8 have been obtained by methylation of N 1 ‐methyl(thiohydrazides) 11 , reaction of 12 with tert ‐butyl carbazate ( 5 ) and deprotection of 13 with HCl/methanol. — Attempts to remove both protecting groups in N 1 ‐alkyl‐ N 2 , N 4 ‐bis