SYNTHESIS AND REDUCTION OF DERIVATIVES OF AZIRIDINEMONO- AND -DICARBOXYLIC ACIDS

Article abstract of DOI:10.1007/BF00506885

Amides and esters of aziridine-2-carboxylic acid were synthesized by the reaction of 1,1,1-trimethyl-2-(2-carboxyethyl)hydrazinium derivatives with an anion-exchange resin or with sodium hydride.Enamines were obtained from 1,1,1-trimethyl-2-<1,2-bis(alkoxycarbonyl)ethyl>hydrazinium salts and basic agents.Methods for the synthesis of amides of aziridine-2,2- and aziridine-2,3-dicarboxylic acids were developed.The stereochemistry of the esters and amides of aziridine-2,3-dicarboxylic acids was established.Dialkylcarbamoylaziridines were reduced with lithium aluminium hydride to 2-(N,N-dialkylaminomethyl)aziridines.The reduction of esters of aziridine-2-carboxylic acid and their functionally substituted derivatives leads to the formation of 2-hydroxymethylaziridines.An O-silylation product was obtained by silylation of 2-hydroxymethylaziridine.