84437-39-8

Upstream product

• 34000-26-5 (2E)-1-(2-hydroxyphenyl)-3-(3-methylphenyl)prop-2-en-1-one 
• 201230-82-2 carbon monoxide 
• 591-17-3 meta-bromotoluene 
• 118-93-4 o-hydroxyacetophenone 
• 766-82-5 1-ethynyl-3-methyl-benzene 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 33675-43-3 1-(bromo-ethynyl)-3-methyl-benzene 
• 90-02-8 salicylaldehyde 
• 533-58-4 2-Iodophenol 
• 13939-06-5 molybdenum hexacarbonyl 
• 42220-75-7 2'-Hydroxy-3-methyl-chalkon 
• 65085-90-7 β,β-dichloro-3'-methyl-styrene 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 108-88-3 toluene 

Downstream Products

• 228088-37-7 2-(3'-bromomethyl-phenyl)-4H-1-benzopyran-4-one 

Relevant academic research and scientific papers

CF3SOCl-promoted intramolecular cyclization of β-diketones: An efficient synthesis of flavones

An efficient intramolecular cyclization reaction of β-diketones containing a phenyl group with an ortho-hydroxyl substituent was achieved. Using CF3SOCl as an additive, the reaction took place under transition-metal-free and mild conditions. A series of flavones were synthesized in moderate to excellent yields.

Temperature-Controlled Stereodivergent Synthesis of 2,2′-Biflavanones Promoted by Samarium Diiodide

In this work, the first example of a radical stereodivergent reaction directed towards the stereoselective synthesis of both (R*,R*)- and (R*,S*)-2,2′-biflavanones promoted by samarium diiodide is reported. Control experiments showed that the selectivity of this reaction was exclusively controlled by the temperature. It was possible to generate a variety of 2,2′-biflavanones bearing different substitution patterns at the aromatic ring in good-to-quantitative yields, being both stereoisomers of the desired compounds obtained with total or high control of selectivity. A mechanism that explains both the generation of the corresponding 2,2′-biflavanones and the selectivity is also discussed. The structure and stereochemistry determination of each isomer was unequivocally elucidated by single-crystal X-ray diffraction experiments.

Rhodium(III)-catalyzed one-pot synthesis of flavonoids from salicylaldehydes and sulfoxonium ylides

Rh(III)-catalyzed C–H activation of salicylaldehyde followed by an insertion reaction with sulfoxonium ylides and cyclization is applied to the synthesis of flavonoids. This one-pot strategy exhibits good functional group tolerance and gives flavones in moderate-to-good yields.

An efficient tandem synthesis of chromones from: O -bromoaryl ynones and benzaldehyde oxime

An effective transition-metal-free strategy was developed for the preparation of chromones from o-bromoaryl ynones and benzaldehyde oxime through sequential C-O bond formation. This cyclization reaction could well tolerate a wide range of functional groups, and the corresponding chromones were given in moderate to excellent yields. Mechanistically, benzaldehyde oxime as a hydroxide source and 1,3-diketone derivatives as reaction intermediates were involved in this transformation.

Novel and Efficient Access to Flavones under Mild Conditions: Aqueous HI-Mediated Cascade Cyclization/Oxidative Radical Reaction of 2-Propynolphenols

Herein we disclose a metal-free and efficient method for the direct conversion of 2-propynolphenols to biologically important flavones using aqueous HI as the promoter. This transformation was proved via 4-iodo-2H-chromenes intermediate, which was simultaneously conversed to corresponding flavones by a Csp2?I bond cleavage and a C–O bond formation under air.

One-pot Synthesis of Aurones through Oxidation-cyclization Tandem Reaction Catalyzed by Copper Nanoparticles Catalyst

Aurones were synthesized through an oxidation-cyclization tandem reaction of 2-(1- hydroxyprop-2-ynyl)phenols catalyzed by copper nanoparticles (Cu NPs) with bipyridine as the ligand. In the reaction, oxygen worked as a green and mild oxidant to give the best results. Cu NPs were dually activated by bipyridine ligand and water, and showed highly efficient catalytic activities to the oxygen oxidation and the cylization to give aurones and flavonoids.

Synthesis and in vitro antioxidant activity study of some novel substituted piperazinyl flavone compounds

Background: A new series of 13 piperazinyl flavone derivatives has been synthesized and examined for their in vitro antiradical and antioxidant activities in response to the pharmacy industry’s increasing demand for new non-toxic anti-inflammatory and anticancer drugs. Method: Their antioxidant activity was evaluated by the reactive oxygen species (ROS) scavenging assays, 2,2-diphenyl-1-picrylhydrazyl free radical (DPPH.) and 2,2'-azino-bis(3- ethylbenzothiazoline-6-sulphonic acid) radical cation (ABTS+.) scavenging assays, and the ferric reducing antioxidant potency (TAC) method, and was compared to known positive controls, herbal infusions, and penicillins. Chemiluminescence, spectrophotometry, electron spin resonance (ESR) and 5,5-dimethyl-1-pyrroline-1-oxide (DMPO) as the spin trap were the measurement techniques. Result: It was seen that synthesized compounds have a wide spectrum of antioxidant property. Some of the test compounds proved to be extremely efficient scavengers of H2O2 exhibiting, in some cases, EC50 of about 2 μM. The values of antioxidant status (TAS) were in the range of 49 ± 3.9 to 1283 ± 51.3 μM TE/g (TE = Trolox equivalent) and were lower than that of butylated hydroxytoluene (BHT) (1304 ± 43.2 μM TE/g) and green tea (1356 ± 40.0 μM TE/g), but for several synthesized compounds, they were higher than chamomille infusion and penicillins. Ferric reducing antioxidant powers (TAC) for the piperazinyl flavone derivatives were in the range 7 ± 0.5 to 104 ± 0.6 μM TE/g and were weaker than that of BHT (217 ± 5.3 μM TR/g). Conclusion: Carboxylic or hydroxamic acid substituted piperazinyl flavones are potentially active as antioxidants, thus may be suggested as pharmacologically interesting ones.

Carbonylative Sonogashira annulation sequence: One-pot synthesis of 4-quinolone and 4H-chromen-4-one derivatives

Carbonylative Sonogashira annulation sequence for one pot synthesis of 4-quinolone and 4H-chromen-4-one has been developed in presence of Pd-NHC catalyst. Substituted 2-iodoaniline and 2-iodophenol independently underwent in the carbonylative Sonogashira

Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes

The palladium-catalyzed intramolecular acylation of alkenyl bromides and aldehydes was developed for an efficient synthesis of 4H-chromen-4-ones. With Pd(PPh3)4/Xphos as the catalyst and K2CO3 as the base, this protocol was applied to synthesize a small library of diversely functionalized flavonoids in moderate to good yields in 1,4-dioxane.

Unified Approach to (Thio)chromenones via One-Pot Friedel-Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones

A facile synthetic method to chromenones and thiochromenones has been developed using a one-pot Friedel-Crafts acylation of alkynes with suitably substituted benzoyl chlorides. This unified approach to (thio)chromenones is readily applicable to aryl- and alkylalkynes where the stereochemically well-defined β-chlorovinyl ketone intermediates undergo distinctively different cyclization pathways. The ready availability of both starting materials, alkynes and benzoyl chlorides, coupled with the experimental simplicity makes the current synthetic method to (thio)chromenones fast, efficient, and practical.