42136-84-5

Basic information

• Product Name: 5(4H)-Oxazolone, 4-(1H-indol-3-ylmethylene)-2-phenyl-
• Synonyms: 4-Indol-3-ylmethylen-2-phenyl-4H-oxazol-5-on;4-indol-3-ylmethylene-2-phenyl-4H-oxazol-5-one
• CAS NO: 42136-84-5
• Molecular Formula: C18H12N2O2
• Molecular Weight: 288.305
• Mol File: 42136-84-5.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 5(4H)-Oxazolone, 4-(1H-indol-3-ylmethylene)-2-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 5(4H)-Oxazolone, 4-(1H-indol-3-ylmethylene)-2-phenyl-(42136-84-5)
• EPA Substance Registry System: 5(4H)-Oxazolone, 4-(1H-indol-3-ylmethylene)-2-phenyl-(42136-84-5)

Safety Data

• Hazardous Substances Data: 42136-84-5(Hazardous Substances Data)

Upstream product

• 98-88-4 benzoyl chloride 
• 495-69-2 Hippuric Acid 
• 22394-31-6 (E)-N-((1H-indol-3-yl)methylene)benzenamine 
• 487-89-8 Indole-3-carboxaldehyde 
• 60777-96-0 (Z)-4-(ethoxymethylene)-2-phenyloxazol-5(4H)-one 
• 120-72-9 indole 
• 24621-70-3 2-(hydroxymethyl)indole 
• 15646-46-5 4-ethoxymethylene-2-phenyl-2-oxazolin-5-one 
• 14848-36-3 4-chloromethylene-2-phenyl-4H-oxazol-5-one 
• 925-90-6 ethylmagnesium bromide 

Downstream Products

• 79722-88-6 methyl Z-2-benzamido-3-(3-indolyl)propenoate 
• 79722-90-0 ethyl (Z)-2-benzoylamino-3-(indol-3-yl)acrylate 
• 75990-09-9 1-Benzoyl-4-hydroxy-5-[1-(1H-indol-3-yl)-meth-(E)-ylidene]-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid methyl ester 
• 134248-30-9 Methyl 4-<4,5-dihydro-4-(1H-indol-3-ylmethylene)-5-oxo-2-phenyl-1H-imidazol-1-yl>benzoate 
• 133363-40-3 4-<3-(1-acetylindolyl)>methylene-2-phenyl-oxazolin-5-one 
• 85622-38-4 (Z)-2-benzamido-3-(indol-3'-yl)propenoic acid 
• 134248-34-3 4-<4,5-Dihydro-4-(1H-indol-3-ylmethylene)-5-oxo-2-phenyl-1H-imidazol-1-yl>benzoic acid hydrazide 
• 134248-40-1 4-{4-[1-(1H-Indol-3-yl)-meth-(Z)-ylidene]-5-oxo-2-phenyl-4,5-dihydro-imidazol-1-yl}-benzoic acid [1-phenyl-meth-(Z)-ylidene]-hydrazide 
• 134248-41-2 4-{4-[1-(1H-Indol-3-yl)-meth-(Z)-ylidene]-5-oxo-2-phenyl-4,5-dihydro-imidazol-1-yl}-benzoic acid [1-(2-hydroxy-phenyl)-meth-(Z)-ylidene]-hydrazide 
• 134248-42-3 4-{4-[1-(1H-Indol-3-yl)-meth-(Z)-ylidene]-5-oxo-2-phenyl-4,5-dihydro-imidazol-1-yl}-benzoic acid [1-(3,4-dimethoxy-phenyl)-meth-(Z)-ylidene]-hydrazide 
• 134248-56-9 4-{4-[1-(1H-Indol-3-yl)-meth-(Z)-ylidene]-5-oxo-2-phenyl-4,5-dihydro-imidazol-1-yl}-benzoic acid [1-phenyl-1-o-tolylazo-meth-(E)-ylidene]-hydrazide 
• 134248-57-0 4-{4-[1-(1H-Indol-3-yl)-meth-(Z)-ylidene]-5-oxo-2-phenyl-4,5-dihydro-imidazol-1-yl}-benzoic acid [1-(4-chloro-phenylazo)-1-phenyl-meth-(E)-ylidene]-hydrazide 
• 134248-58-1 4-{4-[1-(1H-Indol-3-yl)-meth-(Z)-ylidene]-5-oxo-2-phenyl-4,5-dihydro-imidazol-1-yl}-benzoic acid [1-(2-hydroxy-phenyl)-1-o-tolylazo-meth-(E)-ylidene]-hydrazide 
• 134248-59-2 4-{4-[1-(1H-Indol-3-yl)-meth-(Z)-ylidene]-5-oxo-2-phenyl-4,5-dihydro-imidazol-1-yl}-benzoic acid [1-(4-chloro-phenylazo)-1-(2-hydroxy-phenyl)-meth-(E)-ylidene]-hydrazide 

Relevant articles and documents

[Et3NH][HSO4]-mediated functionalization of hippuric acid: an unprecedented approach to 4-arylidene-2-phenyl-5(4H)-oxazolones

A facile, green and stereoselective approach for the synthesis of azlactones/oxazolones 3(a-q) has been developed. The protocol involves reaction of hippuric acid and substituted heterocyclic/aromatic aldehydes in ionic liquid [Et3NH][HSO4] to yield the desired 4-arylidene-2-phenyl-5(4H)-oxazolones in excellent yields (94-97%) with a high degree of purity. The remarkable feature of this pathway is that the ionic liquid eliminates the use of toxic and expensive acetic anhydride and is endowed with catalytic and medium engineering ability. This eco-friendly approach improved synthetic efficiency (94-97% yield), minimizing the production of chemical waste without using highly toxic reagents for the synthesis and more notably, it promoted the selectivity for Z-azlactones/oxazolones. Density functional theory (DFT) calculations revealed that the Z-isomer of compound 3a is stabilised by 2.32 kcal mol-1 more than the E-isomer. This synthetic scheme possesses diverse applicability and is compatible to a range of functional groups (electron donating/electron withdrawing).

Synthesis and anti-inflammatory activity of imidazo[1,2-a] pyridinyl/pyrazinyl benzamides and acetamides

The present study involves synthesis and determination of anti-inflammatory activity of a series of imidazo[1,2-a]pyridinyl/pyrazinyl benzamides and acetamides. Sixteen new imidazo[1,2-a]pyridinyl/pyrazinyl benzamides and acetamides have been prepared by the ring opening of 4-arylidene-2-methyl/ phenyloxazolones with 2-amino azaheterocycles. All the compounds show significant anti-inflammatory activity. The anti-inflammatory activity studies reveal that both acetamide and benzamide derivatives are equally active. Among the two classes of compounds, i.e., imidazo[1,2-a]pyridine and imidazo[1,2-a]pyrazines, the latter show better activity.

2W10O32. 2H2O: A novel and powerful catalyst for the synthesis of 4-arylidene-2-phenyl-5(4)-oxazolones under ultrasonic condition

Di[1,6-bis(3-methylimidazolium-1-yl)hexane] decatungstate dihydrate ([C6(MIm)2]2W10O32. 2H2O) as a new family of polyoxometalate-based dicationic ionic liquids (POM-DIL) is synthesized and employed as a novel and powerful heterogeneous catalyst in the synthesis of 4-arylidene-2-phenyl-5(4)-oxazolones (azlactones) under ultrasound-assisted solvent-free condition. On the basis of the results, the products were obtained in excellent yields under mild condition. Utilization of easy work-up and purification make it very interesting from an economic perspective. Moreover, a recycling study confirmed that the catalyst can be reused multiple times without significant loss of its activity.