250602-55-2

Upstream product

• 2531-80-8 ethyl 2-nitropropionate 
• 617-35-6 2-oxo-propionic acid ethyl ester 

Downstream Products

• 1116585-86-4 ethyl (5Z)-5-(phenylimino)-5H-1,2,3-dithiazole-4-carboxylate 

Relevant academic research and scientific papers

Evaluation of Substituted 1,2,3-Dithiazoles as Inhibitors of the Feline Immunodeficiency Virus (FIV) Nucleocapsid Protein via a Proposed Zinc Ejection Mechanism

A diverse library of 5-thieno-, 5-oxo-, and 5-imino-1,2,3-dithiazole derivatives was synthesized and evaluated for efficacy against the feline immunodeficiency virus (FIV) as a model for HIV in cells. Several diverse compounds from this series displayed n

Iminoxyl radical-based strategy for intermolecular C=O bond formation: Cross-dehydrogenative coupling of 1,3-dicarbonyl compounds with oximes

Cross-dehydrogenative C=O coupling of 13-diketones and 1,3-keto esters with oximes was realized for the first time. The reaction proceeds in the presence of the oxidants [KMnO4, Mn(OAc)2/KMnO4, Mn(OAc)32 H2O, MnO2, Mn(acac)3, Fe(ClO4)3, Cu(ClO4)26 H 2O, Cu(NO3)22.5 H2O, and (NH 4)2Ce(NO3)6]. Twenty cross-coupling products were synthesized using potassium permanganate (KMnO4), manganese(II) acetate dihydrate [Mn(OAc)32 H2O], or the manganese(II) acetate/potassium permanganate [Mn(OAc)2/KMnO 4] system; yields are 27-92%. The synthesis can be easily scaled up to gram quantities of the target products. Apparently, the reaction proceeds via a radical mechanism in which the oxidizing agent serves to generate radicals from oximes and perform the one-electron oxidation of 1,3-dicarbonyl compounds. The formation of oxime radicals was confirmed quantitatively by electron spin resonance (ESR) spectroscopy. The coupling described in the present study is the first example of the selective intermolecular reaction involving unstable iminoxyl radicals generated in situ.

Titanium(IV) enolates of 2-nitrocarboxylic esters and their oxidative chlorinationa convenient route to α-chloro-α-nitrocarboxylates

A new method for the synthesis of 2-chloro-2-nitrocarboxylic esters from 2-nitrocarboxylates is described. The procedure consists of the oxidative chlorination of titanium(IV) enolates of 2-nitro esters in the presence of ammonium nitrate. Esters of 2-chloro-2-nitrocarboxylic acids are formed in very good to quantitative yields. Application of this method for the chlorination of α,α′-dinitrodicarboxylates leads to α,α′- dichloro-α,α′-dinitrocarboxylic esters with high meso-diastereoselectivity. The absence of ammonium nitrate from the reaction mixture affects the reduction of nitro groups and leads to partial transformation of 2-nitrocarboxylic esters into 2-(hydroxyimino)carboxylates. Georg Thieme Verlag Stuttgart - New York.

Indium metal as a reducing agent in organic synthesis

The low first ionisation potential (5.8 eV) of indium coupled with its stability towards air and water, suggest that this metallic element should be a useful reducing agent for organic substrates. The use of indium metal for the reduction of C=N bonds in imines, the heterocyclic ring in benzo-fused nitrogen heterocycles, of oximes, nitro compounds and conjugated alkenes and the removal of 4-nitrobenzyl protecting groups is described. Thus the heterocyclic ring in quinolines, isoquinolines and quinoxalines is selectively reduced using indium metal in aqueous ethanolic ammonium chloride. Treatment of a range of aromatic nitro compounds under similar conditions results in selective reduction of the nitro groups; ester, nitrile, amide and halide substituents are unaffected. Likewise indium in aqueous ethanolic ammonium chloride is an effective method for the deprotection of 4-nitrobenzyl ethers and esters. Indium is also an effective reducing agent under non-aqueous conditions and α-oximino carbonyl compounds can be selectively reduced to the corresponding N-protected amine with indium powder, acetic acid in THF in the presence of acetic anhydride or di-tert-butyl dicarbonate. Conjugated alkenes are also reduced by indium in THF-acetic acid.

Oxyiminoalkanoic acid derivatives with hypoglycemic and hypolipidemic activity

This invention provides a novel oxyiminoalkanoic acid derivative which has excellent hypoglycemic and hypolipidemic actions and which is used for the treatment of diabetes mellitus, hyperlipemia, insulin insensitivity, insulin resistance and impaired glucose tolerance.