Synthesis Of Succinimides Research Articles

Simple and efficient synthesis of N-alkyl and N-aryl succinimides in hot water

ABSTRACTA new, simple synthesis of succinimides is described. The reactions were carried out under the ultimate green conditions excluding both catalyst and organic solvent by applying simple stirring at 100 °C. A wide variety of N-susbstituted succinimides have been prepared in high yields by using succinic acid and primary amines in hot water. Yield of N-alkyl substituted succinimides were found to be higher than those of N-aryl substituted succinimides.

A thermophilic-like ene-reductase originating from an acidophilic iron oxidizer.

Ene-reductases originating from extremophiles are gaining importance in the field of biocatalysis due to higher-stability properties. The genome of the acidophilic iron-oxidizing bacterium "Ferrovum" sp. JA12 was found to harbor a thermophilic-like ene-reductase (FOYE-1). The foye-1 gene was ligated into a pET16bp expression vector system, and the enzyme was produced in Escherichia coli BL21 (DE3; pLysS) cells in yields of 10mgL-1. FOYE-1 showed remarkable activity and rates on N-phenylmaleimide and N-phenyl-2-methylmaleimide (up to 89Umg-1, >97% conversion, 95% (R)-selective) with both nicotinamide cofactors, NADPH and NADH. The catalytic efficiency with NADPH was 27 times higher compared to NADH. At the temperature maximum (50°C) and pH optimum (6.5), activity was almost doubled to 160Umg-1. These findings accomplish FOYE-1 for a valuable biocatalyst in the synthesis of succinimides. The appearance of a thermophilic-like ene-reductase in an acidic habitat is discussed with respect to its phylogenetic placement and to the genomic neighborhood of the encoding gene, awarding FOYE-1 a putative involvement in a quorum-sensing process.

ChemInform Abstract: Solvent‐Induced Reversal of Enantioselectivity in the Synthesis of Succinimides by the Addition of Aldehydes to Maleimides Catalyzed by Carbamate‐Monoprotected 1,2‐Diamines.

AbstractA simple change in the polarity of the solvent allows both enantiomers of substituted succinimides to be obtained in the enantioselective conjugate addition reaction of aldehydes, mainly α,α‐disubstituted, to maleimides catalyzed by chiral carbamate‐monoprotected trans‐cyclohexane‐1,2‐diamines.

Solvent‐Induced Reversal of Enantioselectivity in the Synthesis of Succinimides by the Addition of Aldehydes to Maleimides Catalysed by Carbamate‐Monoprotected 1,2‐Diamines

AbstractA simple change in the polarity of the solvent allows both enantiomers of substituted succinimides to be obtained in the enantioselective conjugate addition reaction of aldehydes, mainly α,α‐disubstituted, to maleimides catalysed by chiral carbamate‐monoprotected trans‐cyclohexane‐1,2‐diamines. Using a single enantiomer of the organocatalyst, both enantiomers of the resulting Michael adducts are obtained in high yields by simply changing the reaction solvent from aqueous DMF (up to 84 % ee) to chloroform (up to 86 % ee). Theoretical calculations are used to explain this uncommon reversal of the enantioselectivity; two transition state orientations of different polarities are differently favoured in polar or nonpolar solvents.

ChemInform Abstract: A Synthesis of Succinimides and Glutarimides from Cyclic Anhydrides.

AbstractAus den aus entsprechenden cyclischen Anhydriden durch Umsetzung mit primären Aminen leicht erhältlichen Dicarbonsäuremonoamiden (I) entstehen mit dem N,N′‐Bis‐succinimidyl‐oxalat (II) über die aktivierten Ester (III) beim Erhitzen in Gegenwart von Dimethylaminopyridin die cyclischen Imide (IV).

A synthesis of succinimides and glutarimides from cyclic anhydrides

The transformation of cyclic anhydrides to their corresponding imides involves a mild three-step sequence: (1) reaction with a primary amine, (2) conversion of the intermediate monoamide to an N-hydroxysuccinimidyl ester using N,N′-disuccinimidyl oxalate (DSO), and (3) cyclization by heating the NHS ester in trichloroethylene in the presence of 4-(dimethylamino)pyridine.

The electrochemical reduction of maleimide: The synthesis of succinimide

The electrochemical reduction of maleimide has been investigated in the pH range 0–14 at a variety of electrode materials. The reaction scheme was found to fall into three distinct sections, depending upon the pH at which the reduction was performed. At low pH the reduction product was found to be succinimide, and the mechanism of its formation is described. At higher pH values, the hydrolysis of starting materials complicates the interpretation of the electrochemical measurements, but nevertheless the overalls reduction mechanism could be deduced. Polarographic data complement information obtained from rotating disc experiments, and comparison is made with the electrochemical reduction of phthalimide.

The electrochemical reduction of maleimide: The synthesis of succinimide

The electrochemical reduction of maleimide has been investigated in the pH range 0–14 at a variety of electrode materials. The reaction scheme was found to fall into three distinct sections, depending upon the pH at which the reduction was performed. At low pH the reduction product was found to be succinimide, and the mechanism of its formation is described. At higher pH values, the hydrolysis of starting materials complicates the interpretation of the electrochemical measurements, but nevertheless the overalls reduction mechanism could be deduced. Polarographic data complement information obtained from rotating disc experiments, and comparison is made with the electrochemical reduction of phthalimide.

Gas-chromatographic determination of maleic anhydride content of products in the synthesis of succinimide additive

Gas-chromatographic determination of maleic anhydride content of products in the synthesis of succinimide additive