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Di-Et 2,3-pyridinedicarboxylates were easily prepared in one pot synthesis by the reaction of EtO₂CCOCHClCO₂Et (I) with α,β-unsaturated aldehydes and ammonia.Especially, di-Et 5-ethyl-2,3-pyridinedicarboxylate (II) was obtained in a good yield (81%) by the reaction of I, 2-ethyl-2-propenal and ammonia in chloroform using an autoclave.In the reaction in an autoclave, the yield of II in chlorobenzene or toluene was similar to that of chloroform.But under atm. pressure, the yield of II was lower in toluene, benzene, and ethanol than in chlorobenzene.

01 Jan 1990·NIPPON KAGAKU KAISHI

Measurement of keto-enol tautomeric equilibrium of oxalacetates by 1H-NMR.

Author: Manabe, Osamu ; Yamashita, Takaharu

Keto-enol tautomeric equilibrium of di-Et oxalacetate (I), dimethyloxalacetate (II), di-Et α-chlorooxalacetate and di-Me α-chlorooxalacetate were determined by ¹H-NMR spectroscopy.Enol tautomers, which were stabilized by intramol. H-bonding to give six-membered rings, existed in almost an E-configuration.In I and II, enolic forms existed in CHCl₃, and the tautomeric equilibrium of I was not altered by changing the temperature or using C₆H₆ as solvent.Keto tautomers were superior to enol in α-chlorooxalacetates since they have only one proton which can be enolized and the enolic forms are destabilized by cross conjugation with +M effect of the chlorine atom.

01 Jan 1981·Journal of Synthetic Organic Chemistry, Japan

最近におけるナフタレン系化合物の用途と合成化学

Author: Mitsuhiro Kodama ; Naokazu Sakota

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