57544-02-2

Usage

InChI:InChI=1/C16H13NO4/c1-20-13-8-6-11(7-9-13)16-14(17(18)19)10-12-4-2-3-5-15(12)21-16/h2-10,16H,1H3

Upstream product

• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 90-02-8 salicylaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 89-95-2 2-methyl-benzyl alcohol 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 

Downstream Products

• 133765-27-2 4-(4-Methoxy-phenyl)-2,3-dimethyl-3,4-dihydro-chromeno[3,4-b]pyrrole-1-carboxylic acid methyl ester 
• 133765-30-7 (Z)-2-[2-(4-Methoxy-phenyl)-3-nitro-chroman-4-yl]-3-methylamino-but-2-enoic acid methyl ester 
• 6889-78-7 4'-(methoxy)-3-hydroxyflavone 
• 100-09-4 4-methoxybenzoic acid 
• 69-72-7 salicylic acid 
• 81289-43-2 2-[3-(4-Methoxy-phenyl)-2-nitro-propyl]-phenol 
• 62232-17-1 2-(4-Methoxy-phenyl)-chroman-3-one 
• 1175542-21-8 4-(4-methoxyphenyl)-1,4-dihydrochromeno[4,3-d][1,2,3]triazole 
• 121824-22-4 (3aS,4R,9bR)-4-(4-Methoxy-phenyl)-2-methyl-3a-nitro-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d]isoxazole 
• 91735-27-2 4,4-Dimethoxy-2-(4-methoxy-phenyl)-chroman-3-one oxime 
• 91735-28-3 3,3-Dimethoxy-2-(4-methoxy-phenyl)-chroman-4-one oxime 

Relevant academic research and scientific papers

Augmentation of Enantioselectivity by Spatial Tuning of Aminocatalyst: Synthesis of 2-Alkyl/aryl-3-nitro-2 H-chromenes by Tandem Oxa-Michael-Henry Reaction

The asymmetric oxa-Michael addition of salicylaldehyde to conjugated nitroalkenes often suffers from poor reactivity and selectivity and a long reaction time. Because of the formation of an iminium ion with aminocatalyst, the nucleophilicity of the phenol

Molecular diversity of the domino annulation reaction of 2-aryl-3-nitrochromenes with pivaloylacetonitriles

In the presence of triethylamine, the domino annulation reaction of two molecules of pivaloylacetonitrile with one molecule of 2-aryl-3-nitrochromene in tetrahydrofuran resulted in the unprecedented imino-substituted dihydrofuro[2,3-c]chromene derivatives in high yields. More importantly, the above domino reaction in refluxing methanol or ethanol afforded alkoxy-substituted chromeno[3,4-b]pyridines in satisfactory yields. However, a similar reaction of benzoylacetonitrile with 2-aryl-3-nitrochromenes in basic medium gave the expected furo[2,3-c]chromene derivatives in moderate yields.

Mild and efficient reductive deoxygenation of epoxides to olefins with tin(II) chloride/sodium iodide as a novel reagent

A highly efficient and green protocol is reported for the reductive deoxygenation of organic epoxides to olefins using tin(II) chloride/sodium iodide as a novel reagent. The reaction gives an excellent yield (85-96%) in ethanol under reflux within 2-10 minutes, without affecting other functional groups. The advantages of our method are the use of inexpensive reagents, the eco-friendly and green reaction conditions, and the short reaction times and high yields.

Bifunctional acid-base ionic liquid for the one-pot synthesis of fine chemicals: Thioethers, 2H-chromenes and 2H-quinoline derivatives

A bifunctional organocatalyst with ionic liquid properties and with an optimized distance between the acid and basic sites efficiently activates electron deficient olefins for 1,4 conjugated addition, which can be incorporated in different one-pot transformations for the preparation of cyclic and acyclic compounds of biological and synthetic interest. More specifically, the catalyst can be successfully applied for different carbon-carbon (CC) and carbon-heteroatom (C-N, C-O, C-S) bond forming reactions integrated in a cascade sequence. The activity of the organocatalyst has been compared with that of structurally related monofunctional and bifunctional catalysts. The most attractive features of this procedure are the high atom economy and the use of inexpensive starting materials as well as the use of an environmentally friendly catalyst that can be easily recovered due to its ionic liquid properties.

Facile access to 2-aryl-3-nitro-2H-chromenes and 2,3,4-trisubstituted chromanes

Using salicylaldehydes and β-nitrostyrenes as starting materials, 2-aryl-3-nitro-2H-chromenes were prepared in good yields (up to 83%) through the combination of 30 mol% of pyrrolidinebenzoic acid catalyzed tandem oxa-Michael-Henry reactions in refluxing

Synthesis, in vitro cytotoxicity and apoptosis inducing study of 2-aryl-3-nitro-2 H -chromene derivatives as potent anti-breast cancer agents

A series of 2-aryl-3-nitro-2H-chromenes 4a-u were designed as hybrid analogs of flavanone, β-nitrostyrene and nitrovinylstilbene scaffolds. They were synthesized from the reaction of appropriate β-nitrostyrenes and salicylaldehydes in good yields. In vitro cytotoxic activities of compounds 4a-u were tested against breast cancer cell lines including MCF-7, T-47D and MDA-MB-231. Most compounds exhibited good cytotoxic activity against selected cell lines, being more potent than standard drug etoposide. Representatively, 8-methoxy-3-nitro-2-(4-chlorophenyl)-2H-chromene (4l) with IC50 Combining double low line 0.2 μ4M against MCF-7 cells, was 36-times more potent than etoposide. Apoptosis as a mechanism of cell death for selected compounds 4h and 4l was confirmed morphologically by acridine orange/ethidium bromide double staining and TUNEL analysis, as well as caspase-3 activation assay.

An expedient synthesis of pyrrolidinyl spirooxindole grafted 3-nitrochromanes through 1,3-dipolar cycloaddition reaction of azomethine ylides

A facile one-pot synthesis of pyrrolidinyl-spirooxindole grafted 3-nitrochromanes has been accomplished by 1,3-dipolar cycloaddition (1,3-DC) reaction of 3-nitrochromenes with azomethine ylides generated in situ from isatin and secondary amino acids. The

Search of antimycobacterial activities in hybrid molecules with benzopyran skeleton

A series of hybrid molecules (7-9, 12, 13, and 14-18) consisting of chromans and pyrolidines or cyclic amines were prepared either by (3 + 2) cycloaddition of nitrostyrenes and azomethine ylide or by three component reactions of chromanyl aldehydes, acetylenes, and cyclic amines. All the synthesized compounds were evaluated against both avirulent (H37Ra) and virulent (H37Rv) strains of Mycobacterium tuberculosis. Out of all the compounds screened, compounds 16, 17, and 18 were found to be active against the virulent strain M. tubercolosis H37Rv displaying MIC in the range of 6.25-1.56 μg/ml against. Springer Science+Business Media, LLC 2010.

Catalyst-free 1,3-dipolar cycloaddition of 3-nitrochromen with sodium azide: a facile method for the synthesis of 4-aryl-1,4-dihydrochromeno[4,3-d][1,2,3]triazole derivatives

1,3-Dipolar cycloaddition of 3-nitrochromen with sodium azide under catalyst-free conditions afforded 4-aryl-1,4-dihydrochromeno[4,3-d][1,2,3]triazole derivatives at 80 °C in DMSO is described. The generality of this reaction was demonstrated by synthesiz

3-Nitrochromene derivatives as 2π components in 1,3-dipolar cycloadditions of azomethine ylides

The 1,3-dipolar cycloaddition of 2-aryl-3-nitrochromenes with various azomethine ylides has been investigated. The structure and stereochemistry of cycloadducts were studied in detail by NMR spectroscopic methods.