32805-76-8

Upstream product

• 141-97-9 ethyl acetoacetate 
• 538-75-0 dicyclohexyl-carbodiimide 
• 108-91-8 cyclohexylamine 

Downstream Products

• 6340-71-2 Ethyl 3-(cyclohexylamino)butyrate 
• 79348-17-7 3-(Cyclohexylamino)-2-(thiobenzoylcarbamoyl)crotonsaeure-ethylester 

Relevant academic research and scientific papers

Tandem Nenitzescu Reaction/Nucleophilic Aromatic Substitution to Form Novel Pyrido Fused Indole Frameworks

5-Hydroxyindoles are privileged structures that form part of various bioactive compounds. The Nenitzescu reaction of quinones and enamines is one of the most powerful methods to obtain 5-hydroxyindoles. In this work, we have applied the Nenitzescu reaction to 2-(2-chloropyrid-3-yl)benzoquinones. Mixtures of regioisomers were obtained that could be separated in the 4- and 6-substituted analogues, and then cyclized separately in a metal-free base-catalyzed reaction, affording novel tetracyclic indole derivatives. These are indeed the first examples reported in the literature of the linear pyrido[3′,2′ : 4,5]furo[3,2-b]indole and angular 1H-pyrido[2′,3′ : 4,5]furo[2,3-c]indole systems. The regioselectivity and the yield of the Nenitzescu reaction were found to be dependent on the N-substituent at the enamine. Furthermore, we analyzed the UV-Vis and PL spectra of the new systems, and this was supported by DFT calculations, allowing us to compare the properties of angular compared to linearly shaped compounds.

Redox Property of Enamines

Enamines are electron-rich compounds bearing intriguing redox properties. Herein, a series of secondary enamines condensed from primary amine and β-ketocarbonyls were synthesized and their electrochemical oxidation properties were systematically studied by cyclic voltammetry. Furthermore, theoretical calculation of oxidation potentials of enamines, particularly those catalytic intermediates, was also conducted to further broaden the scope investigated. Possible structural factors on oxidation and the nature of the resulted radical cation intermediates were revealed and discussed. Correlation of redox potentials with molecular properties such as highest occupied molecular orbital energies and natural population analysis charge were explored, and there appears no simple linear correlation. On the other hand, a good correlation with Mayr's nucleophilicity parameter N was noted among a range of catalytically relevant enamines. Spin population analysis disclosed that enamine radical cations mainly exhibit the carbon-center free radical feature. Taking experimental and computation data together, a comprehensive picture about the redox property of enamines is presented, which would provide guidance in the development of oxidative enamine catalysis and transformations.

Transformation of One-Dimensional Achiral Structure to Three-Dimensional Chiral Structure: Mechanistic Study and Catalytic Activities of Chiral Structure

We have isolated two copper-based coordination polymers through solvent diffusion and solvothermal methods using copper salt, furan dicarboxylic acid (FDC), 4,4′-bipyridine (bpy) in MeOH/ethylene glycol, and water solvents. Compound 1 is adopting P21/c space group and adopts a one-dimensional wirelike structure with a free carboxylate anion. Compound 2 crystallizes in chiral space group P65. This is a three-dimensional structure with helical chains. This helicity might be the reason for chiral generation and symmetry breaking. We have converted compound 1 to compound 2 using grinding, followed by a solvothermal method. The circular dichroism data of 2 showed that it is an enantioenriched compound. We have shown that compound 2 is a very good catalyst for chemo- and regioselective enamination reaction and for azide-alkyne Huisgen cycloaddition, respectively.

Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate

A novel application of highly stable Fe(OTf)3 as an efficient catalyst for the synthesis of a variety of β-enamino ketones and esters under solvent-free conditions is described. Notably, this protocol of a "green synthesis", which produced β-enamino ketones and esters by the reaction of a variety of β-dicarbonyl compounds and primary amines, exhibits attractive properties including high yields, short reaction periods, lower loading of catalyst and chemo- and regio-selectivity. In addition, the catalyst was easily recovered from the reaction system and readily reused with minimal loss of activity.

Zn[aminoacid]2 hybrid materials applied as heterogeneous catalysts in the synthesis of β-enaminones

Hybrid materials have seized attention from scientific community mainly as heterogenic catalysts in organic reactions on a large scale succeeding in some organic compounds with high yields. One of the most important classes of hybrid materials used for this purpose involves the complexation of Zn and aminoacids. Herein, we introduced Zn[Pro]2 and Zn[Gly]2 in the synthesis of several β-enaminones via solvent free protocol and using an ultrasound device.

Zn[aminoacid]2 hybrid materials applied as heterogeneous catalysts in the synthesis of β-enaminones

Hybrid materials have seized attention from scientific community mainly as heterogenic catalysts in organic reactions on a large scale succeeding in some organic compounds with high yields. One of the most important classes of hybrid materials used for this purpose involves the complexation of Zn and aminoacids. Herein, we introduced Zn[Pro]2 and Zn[Gly]2 in the synthesis of several β-enaminones via solvent free protocol and using an ultrasound device.

Zinc triflate catalysed synthesis of β-enamino ketones(esters) under solvent-free conditions

An efficient and mild procedure is described for the synthesis of a series of β-enamino ketones(esters) from 1,3-dicarbonyl compounds and aliphatic and aromatic amines using zinc triflate as the catalyst.

Phosphotungstic acid catalysed synthesis of β-enamino compounds under solvent-free conditions

A convenient eco-friendly procedure has been developed for the synthesis of β-enaminones and β-enamino esters by reacting 1,3-dicarbonyl compounds with amines in the presence of catalytic amounts of phosphotungstic acid (H3PW12O40,1 mol%). The reaction proceeds smoothly at room temperature under solvent-free conditions and gives the corresponding β-enamino compounds in high to excellent yields.

A general and efficient method for the preparation of β-enamino ketones and esters catalyzed by indium tribromide

A variety of β-enamino ketones and esters have been synthesized in high to exellent yields by reacting β-dicarbonyl compounds with amines in the presence of a catalytic amount of indium tribromide. The reaction proceeds smoothly at room temperature in a short reaction time under solvent-free conditions.

Efficient synthetic method for β-Enamino esters catalyzed by Yb(OTf)3 under solvent-free conditions

A wide range of ?-enamino esters have been synthesized in moderate to excellent yields by reacting 1,3-dicarbonyl compounds with amines in the presence of catalytic amounts of Yb(OTf)3 (2 mol%). The reaction proceeds smoothly at ambient temperature under solvent-free conditions. The catalyst can be recovered and reused. CSIRO 2006.