79232-62-5Relevant academic research and scientific papers
Reactions with Aziridines. XXIV: Amidoethylation of Esters of Monosubstituted Malonic Acids
Budny, Jochen,Stamm, Helmut
, p. 657 - 664 (2007/10/02)
Diethyl phenylmalonate (1a) and methylmalonate (1b) have been amidoethylated with the N-acyl aziridines 3a-e under various conditions.In one case only (5) we were able to isolate the primarily formed amidoethyl derivative as minor product which otherwise cyclized apparently completely to form the corresponding N-acyl pyrrolidones 6a-f which mostly underwent further (alcoholytic) reactions.
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.
