Solid-phase synthesis of monocyclic beta-lactam derivatives.
Liquid-phase studies concerning the solid-phase synthesis of monocyclic beta-lactams via the ester-enolate imine condensation route have been conducted utilizing triazene esters 1 and 2 as model compounds. Esters were attached to benzylamine resin 6 by a triazene linker employing the respective diazonium salts. Immobilized ester-enolates 8 and 10 were reacted with various imines and imine precursors to give polymer-bound beta-lactams 14 and 17 in different substitution patterns. Traceless cleavage from the triazene linker yields the desired beta-lactams 16 and 19.
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Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Strasse 1, 52074 Aachen, Germany.
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D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D007202:Indicators and Reagents; D012117:Resins, Synthetic; D047090:beta-Lactams / Q000138:chemical synthesis*
D004952:Esters; D007202:Indicators and Reagents; D012117:Resins, Synthetic; D047090:beta-Lactams