213273-03-1

Basic information

• Product Name: 4H-1-Benzopyran-3-carboxaldehyde, 4-oxo-2-(phenylamino)-
• CAS NO: 213273-03-1
• Molecular Formula: C16H11NO3
• Molecular Weight: 265.268
• Mol File: 213273-03-1.mol

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-3-carboxaldehyde, 4-oxo-2-(phenylamino)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-3-carboxaldehyde, 4-oxo-2-(phenylamino)-(213273-03-1)
• EPA Substance Registry System: 4H-1-Benzopyran-3-carboxaldehyde, 4-oxo-2-(phenylamino)-(213273-03-1)

Safety Data

• Hazardous Substances Data: 213273-03-1(Hazardous Substances Data)

Upstream product

• 113326-75-3 N-((4-oxo-4H-chromen-3-yl)methylene)aniline oxide 
• 79-06-1 2-propenamide 
• 109-92-2 ethyl vinyl ether 
• 118-93-4 o-hydroxyacetophenone 
• 122-79-2 Phenyl acetate 
• 108-95-2 phenol 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 17422-74-1 3-Formylchromone 
• 1219020-15-1 3-(ethylaminomethylene)-2-(N-phenyl)-iminochroman-4-one 
• 113326-75-3 C-(4-oxo-4H<1>benzopyran-3-yl)-N-phenylnitrone 
• 74143-89-8 5-phenyl-3,4-pentadien-2-one 
• 131431-64-6 ethyl hexa-2,3-dienoate 
• 74268-51-2 ethyl 2,3-pentadienecarboxylate 
• 14369-81-4 ethyl 2,3-butadienoate 

Downstream Products

• 547741-46-8 2-{[(2E)-but-2-enyl]phenylamino}-4-oxo-4H-1-benzopyran-3-carboxaldehyde 
• 1173277-76-3 3,3'-methylenebis(2-N-phenylamino-4H-chromen-4-one) 
• 1219020-12-8 2-(N-phenyl)imino-3-(p-tolylaminomethylene)-chroman-4-one 
• 1345096-79-8 3-(2-hydroxybenzoyl)-1-methylquinolin-2(1H)-one 
• 445291-56-5 2-(N-methyl-N-phenyl)aminochromone-3-carboxaldehyde 
• 547741-47-9 4-oxo-2-[N-(phenyl)-N-(3-phenylprop-2(E)-enyl)amino]-4H-1-benzopyran-3-carboxaldehyde 
• 547741-45-7 4-oxo-2-[N-(phenyl)-N-(prop-2-enyl)]amino-4H-1-benzopyran-3-carboxaldehyde 
• 1535170-91-2 4-chloro-3-dichloromethyl-2-(N-phenyl)imino-2H-1-benzopyran 
• 52281-05-7 3-[(phenylamino)methylidene]-3,4-dihydro-2H-1-benzopyran-2,4-dione 

Relevant articles and documents

Investigations on peri-, regio- and stereoselectivities in thermal cycloadditions involving C-(4-oxo-4H[1]benzopyran-3-yl)-N-phenylnitrones: Role of steric factors and secondary interactions in 1,3-dipolar cycloadditions

Complete peri-, regio- and stereoselectivities in thermal reactions of C-(4-oxo-4H[1]benzopyran-3-yl)-N-phenylnitrones with both electron-rich and electron-deficient olefins have been investigated. This conjugated nitrone undergoes frontier-orbital (LUMO-

3-Formylchromone based topoisomerase IIα inhibitors: Discovery of potent leads

Substituted 3-formylchromones were synthesized and evaluated as inhibitors of the human DNA topoisomerase IIα (hTopo-IIα) enzyme. The results of the decatenation, relaxation and DNA intercalation assays revealed that the compounds (11b, 12a, 12b, 12d, 12e, 13a and 13b) exhibited potent inhibitory activity against the hTopo-IIα enzyme, and are nonintercalating agents. These compounds also possess significant in vitro cytotoxicity (LC50 ranges from 0.5-8.6 μM) against prostate (PC-3) cancerous cell line as seen in comparison to the standard drug etoposide. To further probe the plausible mode of action of 3-formylchromone derivatives, molecular docking studies have also been carried out, which showed that the compounds under investigation fitted well in the ATP binding pocket of hTopo-IIα enzyme with good docking scores and form nonbonding interactions with the crucial residues of the catalytic site. The Royal Society of Chemistry.

Exploring α-chromonyl nitrones as 1,5-dipoles

N-Phenyl-C-chromonyl nitrones 1 and the allenoate zwitterion 2, generated by addition of phosphine to acetylenedicarboxylates, undergo a cascade reaction sequence involving an unprecedented [5+3] annulation followed by deoxygenative rearrangement leading to dihydropyridine-fused benzopyrones. Unusual electronic control by the N-substituents of 1 directs the annulation pathway, leading to two different ring-systems. Georg Thieme Verlag Stuttgart - New York.

A one-pot rearrangement of 2-(N-Alkyl-N-aryl)aminochromone-3-carbaldehyde to N-Alkyl-3-salicyloyl-2-quinolone - An antileishmanial agent

2-(N-Aryl)aminochromone-3-carbaldehyde does not show any change on heating in acetic acid, but under the same reaction conditions 2-(N-alkyl-N-aryl) aminochromone-3-carbaldehyde rearranges to 3-salicyloyl-2-quinolones, which exhibits antileishmanial activ

Regio- and stereoselective synthesis of 1-benzopyrano[2,3-b]pyrrolo[2,3-d] pyridines: A microwave-accelerated intramolecular [3+2] cycloaddition reaction of azomethine ylide

Figure represented. Regio- and stereoselective syntheses of tetracyclic compounds having chromone, pyrrolidine, and piperidine rings have been accomplished by an intramolecular [3+2] cycloaddition reaction involving azomethine ylide. The reactions were ca

Reaction of amines with nitrones derived from chromone-3-carbaldehyde

Nitronc 2 derived from 3-formylchromone 1 produces 3-aminomethylene-2- iminochroman-4-one 8 on reaction with primary amine 7, chromenoquinoline 14 with piperidine and dihydrotelraaza[14]annulene 15 with o-phenylenediamine.

Domino routes to substituted benzoindolizines: tandem reorganization of 1,3-dipolar cycloadducts of nitrones with allenic esters/ketones and alternative cycloaddition-palladium catalyzed cyclization pathway

Reactions of C-(4-oxo-4H[1]benzopyran-3-yl)-N-phenyl nitrones (7) with allenic esters (8a-c) and allenic ketones (18a-d) furnish benzoindolizines (9a-k, 19a-d) in good yields. The formation of benzoindolizines is postulated to involve regioselective addit

A one-pot synthesis of 3,3′-methylenebis(2-arylamino-4H-chromen-4-one) from C-(4-oxo-4H-1-benzopyran-3-yl)-N-arylnitrone

2-(Arylamino)-4-oxo-4H-chromene-3-carbaldehyde 3 (R2 = aryl) produces 12H-chromeno[2,3-b]quinolin-12-one 4 when treated with sarcosine, piperidine or diethylamine, but produces 3,3′-methylenebis(2-arylamino-4H-chromen-4-one) 8 when treated with

Intramolecular low-temperature 1,3-dipolar cycloadditions of nitrones: synthesis of chromano-heterocycles

In contrast to the reported facile intramolecular 1,3-dipolar cycloadditions of in-situ generated nitrone on heterocyclic systems, reactions of 2-(N-allyl/crotyl/cinnamyl-anilino)-3-formylchromones with N-phenyl-/methylhydroxylamine under comparable condi

One-pot Synthesis of 2-alkyl/arylamino-4-oxo-4H-1-benzopyran-3-carboxaldehyde from 4-oxo-4H-1-benzopyran-3-carboxaldehyde

Zn/NH4Cl - Mediated reactions of aldehyde 1 with nitro compounds 2 afford 2-(N-alkyl/arylamino)-3-formylchromones 4, which on heating with 70 percent H2SO4 produces 9a-d and 11e-h from 4a-d and 4e-h, respectively.