ChemInform Abstract: SYNTHESIS OF O‐SUBSTITUTED HYDROXYLAMINES

Abstract

Zur Darstellung der O‐substituierten Hydroxylamine (V), die Histidin‐decarboxylaseinhibierende Wirksamkeit besitzen, werden die aus Hydroxyphthalimid (I) und Halogeniden (II) erhältlichen Verbindungen (III) nicht wie üblich mit Hydrazin, sondern vorteilhaft mit prim. Aminen (IV) dephthaloyliert; die Vorteile dieses Verfahrens bestehen in seiner breiten Anwendbarkeit, den milden Reaktionsbedingungen, hohen Ausbeuten sowie der′ Möglichkeit, auch O‐substituierte Hydroxylamine mit Hydrazinempfindlichen Gruppen darzustellen.

A New Supported Reagent for the Parallel Synthesis of Primary and SecondaryO-Alkyl Hydroxylamines through a Base-Catalyzed Mitsunobu Reaction

“…O -Alkyl hydroxylamines are classically obtained either by electrophilic amination of an alcohol − or by alkylation of an N-protected hydroxylamine derivative followed by its deprotection. − We therefore considered adapting one of these solution-phase methods to the solid phase in order to facilitate multiple step synthesis and to have access to high diversity. The strategy consisting of the alkylation of a supported N -hydroxyphthalimide followed by release of the free aminoxy compound in solution by hydrazinolysis or methylaminolysis was selected. Indeed, a large variety of alkylating agents has been described and the volatility of the cleavage reagents allows their easy elimination.…”