131189-26-9

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 62-53-3 aniline 
• 108-56-5 diethyl oxaloacetate 
• 762-21-0 acetylenedicarboxylic acid diethyl ester 
• 4341-76-8 Ethyl 2-butynoate 
• 100-52-7 benzaldehyde 
• 996-82-7 sodium diethylmalonate 
• 836-41-9 p-methoxybenzylidene-phenylamine 

Downstream Products

• 131189-31-6 4-Benzhydryloxy-2-(4-methoxy-phenyl)-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester 
• 131189-36-1 3-Benzhydryl-2-(4-methoxy-phenyl)-4,5-dioxo-1-phenyl-pyrrolidine-3-carboxylic acid ethyl ester 

Relevant academic research and scientific papers

SYNTHESIS, CRYSTAL STRUCTURE, AND DFT STUDIES OF ETHYL 4-HYDROXY-2-(4-METHOXYPHENYL)-5-OXO- 1-PHENYL-2,5-DIHYDRO-1H-PYRROLE-3-CARBOXYLATE

Abstract: An efficient method for the synthesis of a new highly substituted pyrrolidinone derivative is developed via a three-component one-pot reaction of aniline, diethyl acetylenedicarboxylate, and 4-anisaldehyde. The structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate is confirmed by FTIR, 1H and 13C NMR spectroscopy. Unambiguous evidence for the structure of the synthesized product is obtained from the single crystal X-ray analysis. The comparison of both its molecular structure and intermolecular interactions with the previously known analogous compounds reveals that the mutual syn- or antiperiplanar orientation of ester C=O and pyrrolinone-bound OH is related to the type of molecular dimers formed in the solid state. The geometrical structure, the HOMO–LUMO analysis (electrophilicity index), 1H and 13C chemical shifts of the desired product are also calculated by DFT at the B3LYP level with the 6-31++G(d,p) basis set. The calculated chemical shifts are in compliance with the experimental data.

Malic acid as an effective and valuable bioorganocatalyst for one-pot, three-component synthesis of pyrrolidinone derivatives

Malic acid was used as an effective and valuable bioorganocatalyst for the one-pot, three-component synthesis of important and noteworthy pyrrolidinone derivatives in green solvent at 50oC. Ecofriendly, simplicity in operation, cleaner reaction profile, s

Synthesis of Ethyl 3-Methyl-4,5-dioxo-1,2-diphenylpyrrolidine-3-carboxylate Analogues Using Green and Expeditious Grinding Method

Abstract: A specific efficient method of synthesis of biologically active analogues of the title compound from acetylene dicarboxylate, aniline and various aromatic aldehydes catalyzed by citric acid by one-pot mortar-pestle grinding is described. The sho

Green one-pot multicomponent synthesis of pyrrolidinones using planetary ball milling process under solvent-free conditions

This paper presents a novel and efficient protocol for the synthesis of pyrrolidinones using catalytic loading of 1,1'-butylenebis(3-sulfo-3H-imidazol-1-ium) hydrogen sulfate as a recyclable Br?nsted acid ionic liquid through ball milling process at room temperature under solvent-free conditions. The developed method provides good to excellent yields of various pyrrolidinones in environmentally friendly conditions. Furthermore, this efficient protocol displays a combination of the synthetic advantage of one-pot multicomponent reaction with ecological benefits and convenience of a mechanochemical procedure.

Magnetic cobalt ferrite nanoparticles functionalized with citric acid as a green nanocatalyst for one-pot three-component sonochemical synthesis of substituted 3-pyrrolin-2-ones

Abstract: A clean, convenient and facile approach for one-pot ultrasonic assisted synthesis of substituted 3-pyrrolin-2-ones from diethyl acetylenedicarboxylate, aniline and aldehyde derivatives is described. The reactions were carried out in the presence

An Efficient Synthesis of Pyrrolidinone Derivatives in the Presence of 1,1′-Butylenebis(3-sulfo-3 H -imidazol-1-ium) Chloride

The catalytic efficiency of 1,1′-butylenebis(3-sulfo-3H-imidazol-1-ium) chloride as a sulfonic acid-functionalized ionic liquid was demonstrated for the synthesis of pyrrolidinone derivatives under mild conditions. The electronic effect of substituents on aniline derivatives was investigated. Further, a study on the structure-activity relationship of ionic liquids containing sulfonic groups for the synthesis of ethyl-2-(4-chlorophenyl)-4-hydroxy-5-oxo-1-(p-tolyl)-2,5-dihydro-1H-pyrrole-3-carboxylate was performed under optimal conditions. The results showed that the catalytic properties of ionic liquids containing two sulfonic or imidazole moieties with carbon spacers was superior to ionic liquids having one sulfonic or imidazole moiety with no carbon spacer.

In-water facile synthesis of poly-substituted 6-arylamino pyridines and 2-pyrrolidone derivatives using tetragonal nano-ZrO2 as reusable catalyst

Here, we report a facile synthetic protocol to access a series of ethyl 5-cyano-2-methyl-4-aryl-6-(arylamino)nicotinates and ethyl 4-hydroxy-2-(4-nitroaryl)-5-oxo-1-aryl-2,5-dihydro-1H-pyrrole-3-carboxylates using tetragonal nano-ZrO2 as reusab

Admicellar catalysis in multicomponent synthesis of polysubstituted pyrrolidinones

A multicomponent green methodology was developed to synthesize 3-hydroxy-2-pyrrolidinones under admicellar catalysis by TiO2 nano-particles at room temperature (30 C). TiO2 nano-particles in aqueous CTAB solution promote the formation of admicelles and the reaction occurs in admicellar environment. The methodology was successfully applied to synthesize a variety of 3-hydroxy-2-pyrrolidinones and 3′-hydroxyspiro- 2′-pyrrolidinone derivatives.

Enols as feasible acid components in the Ugi condensation

Heterocyclic enols are used for the first time as acid components in an Ugi-type multicomponent condensation. For that purpose, we have chosen enols containing a Michael acceptor, in order to facilitate an irreversible rearrangement of the primary Ugi adduct. The new four-component process leads readily and efficiently to heterocyclic enamines containing at least six elements of diversity.

Molecular diversity of three-component reactions of aromatic aldehydes, arylamines, and acetylenedicarboxylates

The three-component reactions of aromatic aldehydes, arylamines, and acetylenedicarboxylates show very interesting molecular diversity. In an aqueous ethanol solution the three-component reaction gave polysubstituted 2-hydroxyhydropyridines. In absolute ethanol 1,4-dihydropyridines were produced in satisfactory yields. Finally, under acid catalysis, this three-component reaction afforded polysubstituted 2-pyrrolidinones. The reaction mechanism for the formation of the three products is briefly explained. Polysubstituted 2-hydroxyhydropyridines, 1,4-dihydropyridines, and 2-pyrrolidinones were selectively obtained from the multicomponent reactions of aromatic aldehydes, arylamines, and acetylenedicarboxylates.