54396-25-7

Basic information

• Product Name: 2-oxo-N-phenyl-chromene-3-carboxamide
• Synonyms: 2-oxo-N-phenyl-chromene-3-carboxamide;2-oxo-N-phenyl-2H-chromene-3-carboxamide
• CAS NO: 54396-25-7
• Molecular Formula: C₁₆H₁₁NO₃
• Molecular Weight: 265.26344
• Mol File: 54396-25-7.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 539.8°Cat760mmHg
• Flash Point: 280.3°C
• Appearance: /
• Density: 1.369g/cm³
• Vapor Pressure: 1.01E-11mmHg at 25°C
• Refractive Index: 1.683
• CAS DataBase Reference: 2-oxo-N-phenyl-chromene-3-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-oxo-N-phenyl-chromene-3-carboxamide(54396-25-7)
• EPA Substance Registry System: 2-oxo-N-phenyl-chromene-3-carboxamide(54396-25-7)

Safety Data

• Hazardous Substances Data: 54396-25-7(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 22, p. 257, 1985 DOI: 10.1002/jhet.5570220203

InChI:InChI=1/C16H11NO3/c18-15(17-12-7-2-1-3-8-12)13-10-11-6-4-5-9-14(11)20-16(13)19/h1-10H,(H,17,18)

Upstream product

• 110-89-4 piperidine 
• 779-84-0 N-phenylsalicylaldimine 
• 105-53-3 diethyl malonate 
• 90-02-8 salicylaldehyde 
• 886124-83-0 C₁₃H₈N₂O₃ 
• 62-53-3 aniline 
• 1846-76-0 ethyl coumarin-3-carboxylate 
• 1663-67-8 malonoyl dichloride 
• 531-81-7 2-oxo-2H-chromene-3-carboxylic acid 
• 3757-06-0 coumarin 3-carboxylic acid chloride 
• 504-64-3 carbon suboxide 
• 621-10-3 N,N'-diphenylmalonamide 

Downstream Products

• 94-93-9 N,N'-ethylenebis(salicylideneimine) 
• 74556-15-3 N-(4-Bromo-phenyl)-2-[1-(2-nitro-phenyl)-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74556-14-2 N-(4-Bromo-phenyl)-2-[1-(2-hydroxy-phenyl)-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74556-16-4 N-(4-Bromo-phenyl)-2-[1-(4-methoxy-phenyl)-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74568-56-2 N-(4-Bromo-phenyl)-2-[(E)-3-phenyl-prop-2-en-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74556-08-4 N-(4-Bromo-phenyl)-N'-furan-2-ylmethyl-malonamide 
• 74556-13-1 N-(4-Bromo-phenyl)-2-[1-phenyl-meth-(E)-ylidene-hydrazinocarbonyl]-acetamide 
• 74556-07-3 N-(4-Bromo-phenyl)-N'-butyl-malonamide 
• 74556-03-9 N-(4-Bromo-phenyl)-2-hydrazinocarbonyl-acetamide 
• 76152-10-8 N-furfurylsalicylaldimine 
• 2565-54-0 N-salicylidene-butylamine 
• 959-36-4 salicyaldehyde azine 
• 1015066-95-1 C₂₁H₂₀N₂O₇S 
• 1015066-94-0 C₁₉H₁₆N₂O₇S 

Relevant articles and documents

The reaction between an azomethine and malonyl dichloride

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A Primary Amide-Functionalized Heterogeneous Catalyst for the Synthesis of Coumarin-3-carboxylic Acids via a Tandem Reaction

A crystalline primary amide-based bifunctional heterogeneous catalyst, {[Cd2(2-BPXG)(Fum)2(H2O)2]·2H2O}n (1) (where, 2-BPXG = 2,2′-((1,4-phenylenebis(methylene))bis((pyridin-2-ylmethyl)azanediyl)) diacetamide and Fum = fumarate), has been developed for the one-pot synthesis of a series of potentially biologically active coumarin-3-carboxylic acids at room temperature via a Knoevenagel-intramolecular cyclization tandem reaction. Catalyst 1 is prepared at room temperature from a one-pot self-assembly process in 81% yield and high purity within a few hours and has a ladder-like polymeric architecture based on single-crystal X-ray diffraction. Additional characterization of 1 includes elemental analysis, infrared spectroscopy, thermogravimetric analysis, and powder X-ray diffraction. Based on the optimized conditions, it is determined that 1 is highly efficient (conditions: 2 mol % catalyst, 3 h, and 26-28 °C in methanol) for this reaction. Its recyclability up to five cycles without significant loss of activity and structural integrity is also demonstrated. Using both electron-donating and electron-withdrawing substituents on the salicylaldehyde substrate, seven different derivatives of coumarin-3-carboxylic acid were made. Additionally, the monoamine oxidase (MAO) inhibitor, coumarin-3-phenylcarboxamide, has also been synthesized from coumarin-3-carboxylic acid obtained in the catalysis process. A detailed mechanism of action is also provided.

Design, synthesis and antifungal activity evaluation of coumarin-3-carboxamide derivatives

A series of coumarin-3-carboxamides/hydrazides have been designed and synthesized, all the target compounds were evaluated in vitro for their antifungal activity against Botrytis cinerea, Alternaria solani, Gibberella zeae, Rhizoctorzia solani, Cucumber anthrax and Alternaria leaf spot, some of the designed compounds 4a-4g exhibited potential activity in the primary assays, this highlighted by the compounds 4a, 4d, 4e and 4f, EC50 values of which against Rhizoctorzia solani were as low as 1.80 μg/mL, 2.50 μg/mL, 2.25 μg/mL and 2.10 μg/mL, respectively, exhibiting more effective control with that of the positive control than Boscalid. Furthermore, compounds 4a and 4e represented equivalent antifungal activity with Boscalid against Botrytis cinerea.