64450-25-5

Upstream product

• 78-94-4 methyl vinyl ketone 
• 95-53-4 o-toluidine 
• 21911-61-5 N-(2-methylphenyl)glycine 
• 67-64-1 acetone 
• 590-90-9 1-Hydroxy-3-butanone 

Downstream Products

• 13362-80-6 4,8-dimethylquinoline 

Relevant academic research and scientific papers

Biocatalytic Aza-Michael Addition of Aromatic Amines to Enone Using α-Amylase in Water

The Michael addition of amines with enones for synthesizing β-amino carbonyls constitutes a valuable transformation in organic chemistry. While various catalyst have been made available for catalyzing the Michael addition of aromatic amines to enones but

TBN-Catalyzed Dehydrative N-Alkylation of Anilines with 4-Hydroxybutan-2-one

Until now, the substitution of alcohols by N-nucleophiles via TBN-catalyzed dehydrogenation was not known. Herein, we reported a TBN catalyzed dehydrative N-alkylation of anilines with 4-hydroxybutan-2-one in the presence of TEMPO, which was different from the TEMPO/TBN catalyzed oxidation reactions. A range of anilines reacted successfully with 4-hydroxybutan-2-one to generate the N-monoalkylation products in good yields. Mechanistic studies revealed that this reaction most possibly proceeded through aza-Michael addition. Water was the only by-product, making it more environmentally friendly. The gram-scale reactions verified the synthetic practicality of this protocol.

Method for catalyzing N-alkylation reaction by TEMPO and TBN

The invention discloses a method for catalyzing N-alkylation reaction of aniline and 4-hydroxy-2-butanone by TEMPO and TBN. 4-hydroxy-2-butanone and different anilines are used as the reaction substrate, TEMPO (2,2,6,6-tetramethylpiperidine oxide) is used as catalyst, TBN (tert-butyl nitrite) is used as cocatalyst, dimethyl sulfoxide or N,N-dimethylformamide or toluene is used as solvent, N-alkylation product is obtained in nitrogen atmosphere at room temperature, no other by-products are detected. The preparation method of the invention uses TEMPO and TBN to catalyze aniline compounds and 4-hydroxy-2-butanone to perform N-alkylation reaction.

Method for generating beta-amino ketone compounds through iodine catalysis

The invention discloses a method for generating beta-amino ketone compounds by catalyzing 4-hydroxy-2-butanone to react with aromatic amine through iodine. The method comprises the following steps: taking 4-hydroxy-2-butanone and different aromatic amines as reaction substrates, taking iodine as a catalyst, and dimethyl sulfoxide or N,N-dimethyl formamide as a solvent, and reacting at room temperature in a nitrogen atmosphere to obtain the beta-amino ketone compounds, wherein other byproducts are undetected. By adopting the preparation method disclosed by the invention, the beta-amino ketone compounds can be generated by catalyzing 4-hydroxy-2-butanoe to react with aromatic amine through the iodine at room temperature for the first time.

Iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to form β-aminoketones and Benzo[h]quinolones

An iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to yield β-aminoketones and benzo[h]quinolones had been developed. Noble metallic catalysts, oxidants, α β-unsaturated ketone intermediates and aza-Michael addition were not involved in this coupling reaction which made it unique when compared to other reactions reported in literature. Inexpensive iodine catalyst, easy accessible raw materials, mild reaction conditions, good functional group tolerance and excellent selectivity made this coupling reaction be a practical method. This reaction can also be scaled up.

Cobalt-Porphyrin-Catalyzed Intramolecular Buchner Reaction and Arene Cyclopropanation of In Situ Generated Alkyl Diazomethanes

Cobalt(II)-porphyrin catalyzed intramolecular Buchner reaction and arene cyclopropanation of alkyl diazomethanes generated in situ from N-tosylhydrazones gave a range of bicyclic cycloheptatriene fused pyrrolidines and tetracyclic cyclopropane fused pyrro

Practical synthetic strategies towards lipophilic 6-iodotetrahydroquinolines and -dihydroquinolines

The synthesis of novel tetrahydroquinolines (THQ) and dihydroquinolines (DHQ) are reported using three practical, scalable synthetic approaches to access highly lipophilic analogues bearing a 6-iodo substituent, each with a different means of cyclisation. A versatile and stable quinolin-2-one intermediate was identified, which could be reduced to the corresponding THQ with borane reagents, or to the DHQ with diisobutylaluminium hydride via a novel elimination that is more favourable at higher temperatures. Coupling these strongly electron-donating scaffolds to electron-accepting moieties caused the resulting structures to exhibit strong fluorescence.

Amphiphilic methyleneamino synthon through organic dye catalyzed- decarboxylative aminoalkylation

The utilization of a photo-induced synthon generated from N-phenyl glycine by an organic dye and visible light irradiation is disclosed. The intermediate could be coupled with either a radical or a nucleophile in a simple operation to afford several natural product-like compounds.

Anodic generation of a zirconium catalyst for Ferrier rearrangement and hetero Michael addition

An efficient catalyst for Ferrier rearrangement and hetero-Michael addition was successfully generated from a sacrificial zirconium anode into media containing reactants for these reactions. Thus, the catalyst generated, successfully promoted the allylic

Solvent-promoted and -controlled Aza-Michael reaction with aromatic amines

(Chemical Equation Presented) 1,4-Addition of anilines onto Michael acceptors proceeds easily in specific polar protic solvents, without any promoting agent. According to the solvent and to the electrophile, the selectivity of the reaction can be finely tuned. With methyl acrylate as electrophile, only monoaddition takes place in water, while the diadduct is yielded in hexafluoroisopropyl alcohol (HFIP). The use of methyl vinyl ketone as a partner affords the monoadduct in water, the diadduct in trifluoroethanol (TFE), and the quinoline in HFIP.