21854-76-2

Upstream product

• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 1613-90-7 4-methoxy-N-[(E)-phenylmethylidene]aniline 
• 108-94-1 cyclohexanone 
• 100-52-7 benzaldehyde 
• 104-94-9 4-methoxy-aniline 

Downstream Products

• 164026-52-2 2-amino-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 

Relevant academic research and scientific papers

Mannich-type reaction promoted by an ionic liquid

The Mannich-type reaction of silyl enolates with aldimines occurred smoothly with [emim]OTf as a solvent and without the addition of an activator to afford β-amino carbonyl compounds in excellent yields.

Graphene oxide catalytic preparation of β-amino carbonyl compounds method

The invention discloses a method for preparing a beta-amido carbonyl compound through the catalysis of graphene oxide. The method comprises the following step of: directly compounding aromatic aldehyde, aromatic amine and aliphatic ketone under the catalytic action of the graphene oxide by taking water as a solvent to obtain the beta-amido carbonyl compound. According to the method, the used solvent is green and environment-friendly, and a used catalyst is low-cost, nontoxic and stable in the water and air. The preparation method disclosed by the invention is simple, convenient, moderate in reaction condition, short in reaction time and high in beta-amido carbonyl compound yield, and the catalyst, namely the graphene oxide, can be recycled after reaction is finished.

Bronsted acid-surfactant-combined catalyst for the Mannich reaction in water

A series of Bronsted acid-surfactant-combined catalysts (BASCs) functionalised with different acids have been synthesized and applied to catalyze the three-component Mannich reaction with aldehyde, acetone and amine at 25 °C in water. The effects of cation tail length and ions of the ionic liquid and the recyclability of the catalysts and BASC acidity (H0) were investigated. The results demonstrated that the 3-(N,N- dimethyloctylammonium) propanesulfonic acid toluene sulfate ([DOPA][Tos]) provide the best catalytic activity because of the formation of emulsions during the reaction. The catalytic procedure was simple and the catalyst could be recycled 9 times by simple separating processes without noticeably decreasing the catalytic activity. The Royal Society of Chemistry 2014.

Modification of poly(vinyl chloride) with pendant metal complex for catalytic applications

Poly(vinyl chloride) was modified to develop an alternative support for the preparation of polymer-supported catalysts. Commercially available poly(vinyl chloride) was synthetically modified to a polymer containing pendant primary amino groups. The Schiff-base of salicylaldehyde and the amino polymer were prepared and were used as the ligands in the synthesis of a polymer-supported copper complex. The polymer-supported ligand and catalysts were characterized by various physical methods. The polymer with the pendant copper complex was able to catalyze the one-pot three-component Mannich reaction between aldehydes, ketones and anilines under mild and environmentally friendly conditions. The catalyst can be recovered by simple filtration and is reusable.

Heteropoly acid in ionic liquid - An efficient and recyclable system for one-pot three-component Mannich reaction

This paper describes a one-pot three-component Mannich reaction, catalyzed by phosphotungstic acid (H3PW12O40), a heteropoly acid in ionic liquid. The catalyst was found to be mild and efficient, and the protocol affords β-arnino ketones in good yields under ambient conditions. Several ionic liquids and conventional organic solvents were employed for the reaction. The ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([bmim]BF4) offered the best results in terms of yield of the products. It was observed that a Homogeneous reaction medium proved beneficial for the yield of the reaction.

Direct-type catalytic three-component Mannich reaction in aqueous media

Bismuth triflate catalyzed direct-type Mannich reaction of cyclohexanone, aromatic aldehyde, and aromatic amine proceeded smoothly in water to afford the corresponding β-amino ketone with very good yield and moderate to good anti selectivity.

Three-component carbon-carbon bond-forming reactions catalyzed by a Br?nsted acid-surfactant-combined catalyst in water

Reactions of aldehydes, amines, and various nucleophiles such as silyl enolates, ketones, Danishefsky's diene, and allyltribuyltin in water were successfully carried out in the presence of p-dodecylbenzenesulfonic acid (DBSA) as a Br?nsted acid-surfactant-combined catalyst.

Mannich-type reaction catalyzed by dicyanoketene ethylene acetal and the related polymer-supported π-acid: Aldimine-selective reactions in the coexistence of aldehydes

Mannich-type reaction of aldimines and enolsilyl ethers proceeded with excellent aldimine-selectivity in the coexistence of aldehydes by means of dicyanoketene ethylene acetal (DCKEA) and the related polymer-supported dicyanoketene acetal as a recyclable π -acid catalyst.

Mannich-Type Reactions of Aldehydes, Amines, and Ketones in a Colloidal Dispersion System Created by a Bronsted Acid-Surfactant-Combined Catalyst in Water

(matrix presented) Three-component Mannich-type reactions of aldehydes, amines, and ketones were efficiently catalyzed by dodecylbenzenesulfonic acid at ambient temperature in water to give various β-amino ketones in good yields. The same reactions proceeded sluggishly in organic solvents.