94507-50-3Relevant articles and documents
10-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-3-methyl-1H,10H-pyrano[4,3-b] chromen-1-ones from a pseudo-multicomponent reaction and evaluation of their antioxidant activity
Saher, Liza,Makhloufi-Chebli, Malika,Dermeche, Leila,Dermeche, Samia,Boutemeur-Khedis, Baya,Rabia, Cherifa,Hamdi, Maamar,Silva, Artur M.S.
, p. 872 - 879 (2018)
A series of novel 10-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-3-methyl-1H,10H-pyrano[4,3-b]chromen-1-ones were synthesized by a pseudo-three-component reaction of 4-hydroxy-6-methyl-2-oxo-2H-pyran-2-one (TAL) with 2-hydroxyarylaldehydes using different acids as catalysts and solvents. The approach relies on a regioselective cascade reaction involving two molar equiv of the TAL iteratively acting as active methylene in a Knoevenagel condensation and in a Michael addition. The antioxidant activity of the synthesized compounds were determined using the DPPH scavenging assay, being the results dependent on the nature and number of chromone substituents. The compound bearing an ortho-dihydroxy (catechol) moiety showed excellent activity at lower concentrations, while derivatives bearing alkoxy groups as substituents present pro-oxidant activity.
Variability of the Transformations of 4-Hydroxy-6-methyl-2H-pyran-2-one under Modified Biginelli Reaction Conditions
Strashilina,Mazhukina,Fedotova
, p. 102 - 106 (2018/06/14)
A modified version of the three-component Biginelli reaction of 4-hydroxy-6-methyl-2H-pyran-2-one with aromatic aldehydes in urea under conventional heating and microwave activation has been studied. Depending on the order of addition of the reactants, su
The Reactions of 4-Hydroxy-2-pyrones With 2-Hydroxybenzaldehydes. A note of Warning
March, P.,Moreno-Manas, M.,Roca, J. L.
, p. 1371 - 1372 (2007/10/02)
The reaction between 2-hydroxybenzaldehyde and 4-hydroxy-6-methyl-2-pyrone (triacetic acid lactone) affords 3-acetoacetyl-2-chromenone, 7, instead of 3-(2-hydroxybenzylidene)-6-methyl-3,4-dihydro-2H-pyran-2,4-dione, 6.The structures previously reported in the literature for the products formed in the reactions of 4-hydroxy-2-chromenone with 2-hydroxybenzaldehydes in a molar ratio 1:1 are considered erroneous.Thus, the previously reported 3-(2-hydroxybenzylidene)chroman-2,4-dione, 10, should be formulated as 3-(2-hydroxybenzoyl)-2-chromenone, 11.