Schunk S, Enders D
Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Strasse 1, 52074 Aachen, Germany.
J Org Chem. 2002 Nov 15;67(23):8034-42. doi: 10.1021/jo0261552.
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.
利用三氮烯酯1和2作为模型化合物，开展了关于通过酯-烯醇盐亚胺缩合路线进行单环β-内酰胺固相合成的液相研究。通过使用相应的重氮盐的三氮烯连接基，将酯连接到苄胺树脂6上。固定化的酯-烯醇盐8和10与各种亚胺和亚胺前体反应，以不同的取代模式得到聚合物负载的β-内酰胺14和17。从三氮烯连接基上无痕裂解得到所需的β-内酰胺16和19。
