13252-79-4

Basic information

• Product Name: 3-Acetoacetylcoumarin
• Synonyms: 3-Acetoacetylcoumarin
• CAS NO: 13252-79-4
• Molecular Formula: C₁₃H₁₀O₄
• Molecular Weight: 0
• Mol File: 13252-79-4.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Acetoacetylcoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Acetoacetylcoumarin(13252-79-4)
• EPA Substance Registry System: 3-Acetoacetylcoumarin(13252-79-4)

Safety Data

• Hazardous Substances Data: 13252-79-4(Hazardous Substances Data)

Upstream product

• 3949-36-8 3-acetylcoumarin 
• 64-19-7 acetic acid 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 90-02-8 salicylaldehyde 
• 7637-07-2 boron trifluoride 
• 108-24-7 acetic anhydride 
• 89-95-2 2-methyl-benzyl alcohol 

Downstream Products

• 1309791-68-1 2-(7-hydroxy-7-methyl-2,3,4,7-tetrahydro-1,4-oxazepin-5-yl)-3-(2-hydroxyphenyl)acrylic acid 
• 1413442-25-7 11a-hydroxy-4-(4-methoxyphenyl)-4,4a,11a,12-tetrahydro-2H-chromeno[3,2-g]quinazoline-2,5(3H)-dione 
• 1413442-24-6 11a-hydroxy-4-phenyl-4,4a,11a,12-tetrahydro-2H-chromeno[3,2-g]quinazoline-2,5(3H)-dione 

Relevant articles and documents

One-pot multicomponent synthesis of novel 1-thiazolyl-5-coumarin-3-yl-pyrazole derivatives and evaluation of their cytotoxic activity

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 novel and direct synthetic route to substituted 1,5-dihydro-4H- [1]benzopyrano[4,3-b]pyridine-4,5-diones

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.

Variability of the Transformations of 4-Hydroxy-6-methyl-2H-pyran-2-one under Modified Biginelli Reaction Conditions

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

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

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.