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Reaktionen mit Aziridinen (Aziranen), XXVI. Aminkatalysierte Amidoethylierungen von β-Dicarbonylverbindungen Eine einfache Synthese von 2-Methylpyrrol-1,3-dicarbonester
Stamm, Helmut,Gailius, Viktor
, p. 3599 - 3608 (2007/10/02)
Esters of nonsubstituted and monosubstituted malonic, cyanoacetic, and β-keto acids are easily C-amidoethylated by N-acylaziridines in the presence of triethylamine.In this amine catalyzed reaction the acylaziridines show different degrees of reactivity.Often the products cannot be obtained by the known amidoethylation procedure or but in smaller yields.The new products 3g may smoothly be converted to the pyrroline 9 and further to the 2-methylpyrrole-1,3-dicarboxylate 10. - Divergent from earlier results, the primary amidoethylation product can be isolated from the known sodium salt reaction of tert-butyl acetoacetate with nonbulky acylaziridines.This product is cleaved by trifluoroacetic acid with remarkable easiness to yield the corresponding amidoethyl derivate of acetone.
