77038-25-6

Upstream product

• 34000-26-5 (2E)-1-(2-hydroxyphenyl)-3-(3-methylphenyl)prop-2-en-1-one 
• 1101612-82-1 C₂₁H₂₂O₄ 
• 118-93-4 o-hydroxyacetophenone 
• 491-38-3 1-benzopyran-4(4H)-one 
• 591-17-3 meta-bromotoluene 
• 620-23-5 m-tolyl aldehyde 
• 42220-75-7 2'-Hydroxy-3-methyl-chalkon 

Downstream Products

• 534569-46-5 C₁₇H₁₇N₃O₂ 
• 34000-26-5 (2E)-1-(2-hydroxyphenyl)-3-(3-methylphenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Direct α-Arylation/Heteroarylation of 2-Trifluoroboratochromanones via Photoredox/Nickel Dual Catalysis

Utilizing photoredox/nickel dual catalysis, diverse flavanones have been synthesized by coupling novel 2-trifluoroboratochromanone building blocks with aryl and heteroaryl bromide partners. The newly reported trifluoroboratochromanones can be easily accessed from the corresponding chromones on multigram scale. This represents a general route for accessing natural and unnatural flavanones that were previously formed through a synthetically more restrictive ring closure route from chalcone precursors.

Synthesis, crystal structure and antitumour activity evaluation of 1H-thieno[2,3-c]chromen-4(2H)-one derivatives

A series of 1H-thieno[2,3-c]chromen-4(2H)-one derivatives were synthesised through Knoevenagel condensation of substituted flavanones with thiazolidine-2,4-dione in ethanol in the presence of piperidine. The mechanism of the reaction was proposed. All synthesised compounds were characterised by IR, 1H NMR, 13C NMR, HRMS, and elemental analysis. The structure of 2-(3-chlorophenyl)-1H-thieno[2,3-c]chromen-4(2H)-one was confirmed by a single crystal X-ray diffraction analysis. A preliminary antitumour screening showed that 2-(2-fluorophenyl)-1H-thieno [2,3-c]chromen-4(2H)-one had moderate to good activity against A549, BGC-823, HCT116 and MDA-MB-453 cancer cell lines, and 2-(3,4-dimethoxyphenyl)-1H-thieno[2,3-c]chromen-4(2H)-one displayed similar activity against these four kinds of cancer cells compared with the reference drug.

Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to chromones: A highly enantioselective pathway for accessing chiral flavanones

Chromone has been noted to be one of the most challenging substrates in the asymmetric 1,4-addi-tion of α,β-unsaturated carbonyl compounds. By employing the rhodium complex associated with a chiral diene ligand, (R,R)-Ph-bod, the 1,4-addition of a variety of aryl-boronic acids was realized to give high yields of the corresponding flavanones with excellent enantioselectivities (≥97% ee, 99% ee for most substrates). Ring-opening side products, which would lead to erosion of product enantioselectivity, were not observed under the stated reaction conditions.

Asymmetric intramolecular oxa-Michael addition of activated α,β-unsaturated ketones catalyzed by a chiral N,N′-dioxide nickel(II) complex: Highly enantioselective synthesis of flavanones

(Chemical Equation Presented) The title reaction provides a promising approach for the synthesis of chiral flavanones with broad substrate scope and is tolerant to air and moisture. Good to excellent enantioselectivities and high yields were achieved for most substrates under mild conditions.

A concerted synthesis of hydroxychalcones, flavanones and benzo[b]furans through palladium-catalysed reactions

A convenient palladium-catalysed procedure for the synthesis of o-hydroxychalcones, flavanones and benzo[b]furans is described where o-iodophenyl acetate was used as a common precursor.

Thermal Isomerization Equilibrium between 2'-Hydroxychalcones and Flavanones

Nine substituted 2'-hydroxychalcones and the corresponding flavanones were heated separately at 230 +/- 0.2 deg C in nitrogen atmosphere.Both materials were mutually isomerized under these reaction conditions and the equilibrium constants of this isomerization were measured by means of HPLC analyses.The substituent effect on the equilibrium is discussed and thermodynamic functions (ΔG, ΔH, and ΔS) are calculated.

3-Methylene flavanones and 3-methylene chromanones

Compounds which are 3-methylene flavanones and 3-methylene chromanones having activity against microorganisms are disclosed. The compounds are represented by the general structural formula: STR1 wherein: R1 is a member selected from the group consisting of hydrogen, Br, CH3 and OCH3 ; R2 is selected from the group consisting of hydrogen and STR2 wherein R4 is a member selected from the group consisting of hydrogen, Br, Cl, CH3, OCH3, NO2, N(CH3)3 and CN; R5 is selected from the group consisting of hydrogen and Cl, with the proviso that when R5 is Cl, R4 is hydrogen or Cl; and R3 is selected from the group consisting of hydrogen, phenyl, 2-thienyl, 4-pyridyl and naphthyl, with the proviso that when R3 is naphthyl, R1 and R2 are hydrogen.