1564-29-0

Usage

Uses

Used in Organic Synthesis:
4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one is used as a key intermediate in organic synthesis for the development of new materials and bioactive compounds. Its unique structure allows for versatile chemical reactions, facilitating the creation of a wide range of organic molecules with potential applications in various industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one is utilized as a chiral building block for the synthesis of enantiomerically pure drugs. Its ability to recognize chirality is crucial for the production of pharmaceuticals with specific biological activities, ensuring the desired therapeutic effects and minimizing side effects.
Used in Chiral Separation and Analysis:
4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one is employed as a chiral selector in chromatographic techniques for the separation of enantiomers. Its chiral recognition properties are instrumental in distinguishing between different stereoisomers of chiral compounds, which is essential for the purity and efficacy of pharmaceuticals and other chiral molecules.
Used in Material Science:
In the field of material science, 4-[4-(Dimethylamino)benzylidene]-2-phenyl-2-oxazolin-5-one is used as a component in the design and synthesis of advanced materials with specific properties. Its incorporation into polymers, for instance, can lead to materials with tailored characteristics such as improved stability, selectivity, or responsiveness to environmental stimuli.

InChI:InChI=1/C18H16N2O2/c1-20(2)15-10-8-13(9-11-15)12-16-18(21)22-17(19-16)14-6-4-3-5-7-14/h3-12H,1-2H3/b16-12+

Upstream product

• 495-69-2 Hippuric Acid 
• 108-24-7 acetic anhydride 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 104-87-0 4-methyl-benzaldehyde 
• 103-72-0 phenyl isothiocyanate 
• 101306-91-6 sodium 1-hydroxy-1-(4-dimethylaminophenyl)methanesulfonate 
• 532-94-5 sodium hippurate 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 
• 1199-01-5 2-phenylazlactone 
• 889-37-2 N,N-dimethyl-4-((phenylimino)methyl)aniline 
• 15646-46-5 4-ethoxymethylene-2-phenyl-2-oxazolin-5-one 
• 14848-36-3 4-chloromethylene-2-phenyl-4H-oxazol-5-one 
• 121-69-7 N,N-dimethyl-aniline 

Downstream Products

• 141212-43-3 (Z)-2-amino-4-p-dimethylaminobenzylidene-2-imidazolin-5-one 
• 144809-96-1 N-[(5S,6S)-6-(4-Dimethylamino-phenyl)-4-oxo-2-thioxo-3-o-tolyl-[1,3]thiazinan-5-yl]-benzamide 
• 144809-95-0 N-[(5R,6R)-6-(4-Dimethylamino-phenyl)-4-oxo-3-phenyl-2-thioxo-[1,3]thiazinan-5-yl]-benzamide 
• 144809-97-2 N-[(5S,6S)-6-(4-Dimethylamino-phenyl)-3-naphthalen-1-yl-4-oxo-2-thioxo-[1,3]thiazinan-5-yl]-benzamide 
• 144810-00-4 Naphthalen-1-yl-dithiocarbamic acid (R)-(4-dimethylamino-phenyl)-((R)-5-oxo-2-phenyl-4,5-dihydro-oxazol-4-yl)-methyl ester 
• 107399-72-4 (Z)-4-(4-(dimethylamino)benzylidene)-1,2-diphenyl-1H-imidazol-5(4H)-one 
• 82301-69-7 (Z)-N-benzoylamino-3-(4-dimethylaminophenyl) acrylic acid methyl ester 
• 99855-77-3 (4-(N,N-dimethylamino)phenyl)pyruvic acid 
• 669775-19-3 methyl (N-benzoyl)-4'-dimethylaminophenylalaninate 
• 59591-90-1 (Z)-5-(4-(dimethylamino)benzylidene)-2-phenyl-3,5-dihydro-4H-imidazol-4-one 
• 1352220-98-4 N-{(Z)-1-(methylcarbamoyl)-2-[4-(dimethylamino)phenyl]vinyl}benzamide 
• 1352221-02-3 N-[(Z)-1-(cyclopropylcarbamoyl)-2-(4-(dimethylamino)phenyl)vinyl]benzamide 
• 1206798-94-8 C₂₆H₂₁ClN₆OS₂ 
• 1246511-72-7 C₂₄H₂₁N₅O₂ 

Relevant academic research and scientific papers

Synthesis and luminescence properties of analogues of the green fluorescent protein chromophore

The green fluorescent protein (GFP) is extensively used as a biomarker for fluorescence biological imaging. The chromophore in GFP is only fluorescent when confined into the β–barrel of the protein. Similarly, synthetic analogues of the fluorophore of GFP

Discovery of a necroptosis inhibitor improving dopaminergic neuronal loss after mptp exposure in mice

Parkinson’s disease (PD) is the second most common neurodegenerative disorder, mainly characterized by motor deficits correlated with progressive dopaminergic neuronal loss in the substantia nigra pars compacta (SN). Necroptosis is a caspase-independent f

Benzothiazol clubbed imidazol-4-ones as anti-fungal, anti-tubercular and anti-HIV-1 agents: Their synthesis and molecular docking study

Background: The present work describes antimicrobial, antimycobacterium and anti HIV-1 evaluation of newly synthesized 5-(4-Substituted-benzylidene)-3-[4-(5-methyl-benzothiazol2-yl)-phenyl]-2-phenyl-3,5-dihydro-imidazol-4-one (4a-o). The docking studies were performed in order to predict the potential binding affinities. Objective: The major aim of this study is to develop the new class of bezylidine candidate clubbed with benzothiazole with less toxicity and improved potency as antimicrobial, antitubercular and anti HIV-1. Methods: The titled compounds were characterized by spectral studies (IR, 1H NMR, 13C NMR and Mass). In vitro antimycobacterium activity was carried out using Lowenstein-Jensen medium method and antimicrobial activity using the broth microdilution method. The anti HIV-1 reverse transcriptase activity was determined by the colorimetric MTT method and inhibition of virusinduced cytopathogenicity in MT-4 cells. Results: Compound 4i (50 μM) showed better antifungal activity against A. clavatus. Compound 4g (50 μM) with 95% inhibition demonstrated good activity against M. tuberculosis H37Rv. Compound 4k showed CC50 (50 μM) against MT-4 (CD4+ Human T-cells containing an integrated HTLV-1 genome) cells by 50%, while 16 μM concentration value EC50 from the HIV-1 induced cytopathogenicity. Molecular docking study suggested that 4k interacted with the target with binding energy by Vina score (-10.3 Kcal/mol) Conclusion: The preliminary in vitro evaluation results revealed that some of the compounds have promising antimicrobial activities as well as antitubercular potency. Among the various substituents on benzylidene, the nitro group was the most beneficial for improving the anti-HIV-1 activity. Docking result suggested that 4k compound could be acting as a non-competitive or weak inhibitor of Reverse Transcriptase (RT).

Synthesis and herbicidal activity of 4-benzylidene-2-phenyl oxazol-5(4H)-one derivatives using l-proline as catalyst

A simple, efficient and environmentally benign method for the synthesis of 4-benzylidene-2-phenyl oxazol-5(4H)-one derivatives by the reaction of aromatic aldehydes and hippuric acid using acetic anhydride as dehydrating agent and L-proline as catalyst ha

An ionic liquid gel: A heterogeneous catalyst for Erlenmeyer-Plochl and Henry reactions

An ionic liquid gel has been prepared by entrapping 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) in an aqueous agar gel. The ionic liquid gel has been characterized by Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). The ionic liquid gel has been successfully employed as a heterogeneous catalyst in the Erlenmeyer-Plochl reaction involving aldehydes, hippuric acid and acetic anhydride as well as in the Henry reaction between aldehydes and nitromethane in ethanol at room temperature. The heterogeneity of the ionic liquid gel has been confirmed by conducting hot filtration tests and leaching studies. Additionally, the ionic liquid gel could be easily recovered by simple filtration and reused five times without significant loss in catalytic activity.

Sulfanilic acid-catalyzed green synthesis of 4-Arylidene-2-phenyl-5(4H)-Oxazolones

This study is focused on the catalytic activity of sulfanilic acid (SA) in the straightforward synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones via condensation of aromatic aldehydes, hippuric acid, and acetic anhydride under green experimental conditio

Greener approach: Ionic liquid [Et3NH][HSO4]-catalyzed multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones under solvent-free condition

We have developed simple, greener, safer multicomponent synthesis series of 4-arylidene-2-phenyl-5(4H) oxazolones 4(a-r) catalyzed by Bronsted acid ionic liquid as triethylammonium hydrogen sulfate [Et3NH][HSO4] and catalytic amount of acetic anhydride and sodium acetate with excellent yields (90–99%). The protocol offers economical, environmentally benign, solvent-free conditions, and recycle–reuse of the catalyst and easily available starting as benzoyl chloride 1, amino acid 2 and a variety of aldehydes 3. The cyclization followed by condensation of benzoyl chloride, amino acid, and a variety of aldehydes catalyzed by ILs [Et3NH][HSO4] and catalytic amount of acetic anhydride and sodium acetate. The final products were confirmed by their characterization data such as FTIR, 1H-NMR, 13C-NMR, Mass, high-resolution mass spectra and were compared with its reported method.

Triphenylphosphine (PPh3) Catalyzed Erlenmeyer Reaction for Azlactones under Solvent-free Conditions

This study presents triphenylphosphine catalyzed process for the synthesis of azlactones and their derivatives using hippuric and substituted aromatic aldehydes. The methodology also found to be effective for the synthesis of azlactones from 5-(2,6-dichlorophenyl)-3-methyl-1,2-oxazol-4-yl carbonyl amino acetic acid and offers several advantages such as solvent-free conditions, excellent yields, simple procedure, mild conditions, and reduced environmental consequences.

Synthesis of Erlenmeyer-Pl?chl azlactones promoted by 5-Sulfosalicylic acid

5-Sulfosalicylic acid was found as an efficient catalyst in the synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones by condensation and cyclodehydration of aromatic aldehydes with hippuric acid and acetic anhydride at room temperature. The catalyst was eas

Microwave-assisted efficient synthesis of azlactones using zeolite NaY as a reusable heterogeneous catalyst

The efficient preparation of azlactones in the presence of zeolite NaY has been reported. This heterogeneous catalyst was used for efficient synthesis of azlactone derivatives with Ac2O as a condensing agent under microwave irradiation and solvent-free co