13252-79-4Relevant articles and documents
One-pot multicomponent synthesis of novel 1-thiazolyl-5-coumarin-3-yl-pyrazole derivatives and evaluation of their cytotoxic activity
Velpula, Ravibabu,Deshineni, Rajitha,Gali, Rajitha,Bavantula, Rajitha
, p. 1729 - 1740 (2016)
A series of novel 1-thiazolyl-5-coumarin-3-yl-pyrazole derivatives (4a-l) were synthesized via one-pot multicomponent reaction of 5-substituted salicylaldehydes (1a-c), 4-hydroxy-6-methyl-2H-pyran-2-one (2) and 2-hydrazinyl-4-arylthiazoles (3a-d) in acetonitrile using a catalytic amount of piperidine under reflux conditions. This multicomponent approach has advantages such as reduced reaction time and a high product yield percentage when compared with corresponding multistep approaches. All the synthesized compounds were evaluated for their cytotoxic activity against Hep G2 (hepatocellular liver carcinoma) and MCF-7 (breast cancer) cell lines and compared with the standard drug Doxorubicin. Among all the compounds, compounds 4d against Hep G2, 4k against MCF-7 and 4e against both Hep G2 & MCF-7 showed excellent cytotoxic activity.
A highly sensitive and selective off–on fluorescent chemosensor for hydrazine based on coumarin β-diketone
Wu, Wei-Na,Wu, Hao,Wang, Yuan,Mao, Xian-Jie,Zhao, Xiao-Lei,Xu, Zhou-Qing,Fan, Yun-Chang,Xu, Zhi-Hong
, p. 80 - 84 (2018)
A coumarin-based sensor C1, namely 3-acetoacetylcoumarin was designed, synthesized and applied for hydrazine detection. Hydrazinolysis of the chemosensor gives a fluorescent coumarin-pyrazole product C1???N2H4 [3-(3-methyl-1H-pyrazol-5-yl)coumarin], and thus resulting in a prominent fluorescence off-on response toward hydrazine under physiological conditions. The probe is highly selective toward hydrazine over cations, anions and other biologically/environmentally abundant analytes. The detection limit of the probe is 3.2?ppb. The sensing mechanism was supported by 1H NMR, IR, MS and DFT calculation. The application of the fluorescent probe in monitoring intracellular hydrazine in glioma cell line U251 was also demonstrated.
A novel and direct synthetic route to substituted 1,5-dihydro-4H- [1]benzopyrano[4,3-b]pyridine-4,5-diones
Svetlik, Jan,Pronayova, Nad'a,Hanus, Vladimir
, p. 395 - 399 (2000)
The condensation of 4-hydroxy-6-methyl-2H-pyran-2-one and substituted 2- hydroxybenzaldehydes with ammonium acetate gave the title heterocycles. Synthesis of 1,5-dihydro-2-methyl-4H-[1]naphtho[1',2':5,6]pyrano[4,3-b]- pyridine-4,5-dione is also described. A reaction mechanism is discussed.
Ionic liquid, [bmim]Br, as an efficient promoting medium for synthesis of 3-acetoacetylcoumarin derivatives without the use of any catalyst
Shi, Da-Qing,Zhou, Yao,Rong, Shao-Feng
, p. 3500 - 3508 (2009)
A series of 3-acetoacetylcoumarin derivatives were synthesized via the reaction of substituted 2-hydroxybenzaldehydes and 4-hydroxy-6-methyl-2H-pyran- 2-one in ionic liquid. This method has the advantages of good yields, milder reaction conditions, easier workup, no catalyst, and environmentally benign procedure.
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)
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
Synthesis of xanthene and coumarin derivatives in water by using β-Cyclodextrin
Kamat, Siddharth R.,Mane, Ananda H.,Patil, Audumbar D.,Lohar, Trushant R.,Salunkhe, Rajashri S.
, p. 911 - 924 (2020/11/09)
Simple and green procedure was developed for the synthesis of various xanthene and coumarin derivatives using beta-cyclodextrin (β-CD) as reusable catalyst at 70?°C in water. Condensation of salicylaldehyde (1?mmol) and dimedone (2?mmol) or 1,3 cyclohexadione (2?mmol) gave corresponding xanthene derivatives, while condensation of salicylaldehyde (1?mmol) with Meldrum’s acid (1?mmol) or 4-Hydroxy-6-methyl-2H-pyran-2-one (1?mmol) gave respective coumarin derivatives in impressive yields. Involvement of β-CD as catalyst was ascertained by inclusion complex evaluation of β-CD-salicylaldehyde with 1H NMR analysis at 70?°C. Graphic abstract: [Figure not available: see fulltext.].
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 (2018/01/22)
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.
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.
