5950-35-6Relevant academic research and scientific papers
AMMONOLYSIS OF AZIRIDINECARBOXYLIC ACID ESTERS
Trapentsier, P. T.,Kalvin'sh, I. Ya.,Liepin'sh, E. E.,Lukevits, E. Ya.
, p. 283 - 285 (1983)
The ammonolysis of 1-(2-methoxycarbonylvinyl)- and 1-(1,2-dimethoxycarbonylvinyl)-2-methoxycarbonylaziridines at normal pressure leads to 1-(2-methoxycarbonylvinyl)- and 1-(1,2-dicarbamoylvinyl)-2-carbamoylaziridines, respectively, whereas 1,3-diazabicyclohexan-4-one derivatives are formed under pressure.
2-Substituted Penems with Amino Acid-Related Side Chains: Synthesis and Antibacterial Activity of a New Series of β-Lactam Antibiotics
Altamura, Maria,Perrotta, Enzo,Sbraci, Piero,Pestellini, Vittorio,Arcamone, Federico,et al.
, p. 4244 - 4256 (2007/10/03)
A new series of 6-(hydroxyethyl)penems 2-substituted with amino acid-related side chains was synthesized.The nature of the amino acyl derivative proved to be crucial both from a synthetic point of view, as β-lactam ring opening can compete with C-2 nucleophilic substitution, and for antibacterial activity.Primary amino acid amides emerged as the most suitable side chains for enhancing permeability through a Gram-negative outer membrane.In vitro activity of the new 2-penems 3a-u was influenced by the nature and position of the amide moiety, the ring size for cyclic amides, and the configuration of the amino acid.Compounds bearing amides derived from small N-methyl amino acids (such as 3a) or from cyclic amino acids (such as prolinamide 3p and 4-hydroxyprolinamide 3r) showed broad spectrum in vitro activity against both Gram-positive and Gram-negative microorganisms.
SYNTHESIS AND REDUCTION OF DERIVATIVES OF AZIRIDINEMONO- AND -DICARBOXYLIC ACIDS
Trapentsier, P. T.,Kalvin'sh, I. Ya.,Liepin'sh, E. E.,Lukevits, E.
, p. 982 - 989 (2007/10/02)
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-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.
