31913-41-4

Upstream product

• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 186032-77-9 6-methyl-4-(phenylethynyl)pyran-2-one 
• 811862-80-3 4-(4-fluorophenyl)-6-methyl-2H-pyran-2-one 
• 872452-03-4 N-(1-(6-methyl-2-oxo-2H-pyran-4-yl)vinyl)acetamide 
• 4467-33-8 6-methyl-4-phenyl-2H-pyran-2-one 
• 67075-01-8 4-(4-methoxy-phenyl)-6-methyl-pyran-2-one 
• 1172631-96-7 4-(4-cyanophenyl)-6-methyl-2H-pyran-2-one 
• 1334224-68-8 6-methyl-4-[4-(trifluoromethoxy)phenyl]-2(2H)-pyranone 
• 1434146-79-8 N-benzyl-2,2-dichloro-N-(6-methyl-2-oxo-2H-pyran-4-yl)acetamide 
• 1434146-84-5 4-(benzylamino)-3-(2,2-dichloroacetyl)-6-methyl-2H-pyran-2-one 
• 1434146-80-1 N-benzyl-N-(6-methyl-2-oxo-2H-pyran-4-yl)isobutyramide 
• 1434146-86-7 4-(benzylamino)-3-isobutyryl-6-methyl-2H-pyran-2-one 
• 727664-07-5 4-(benzylamino)-6-methyl-3-propionyl-2H-pyran-2-one 
• 1434146-90-3 4-(benzylamino)-3-(2-bromopropanoyl)-6-methyl-2H-pyran-2-one 
• 234774-85-7 4-(benzylamino)-6-methyl-2H-pyran-2-one 

Relevant academic research and scientific papers

Triacetic acid lactone as a common intermediate for the synthesis of 4-hydroxy-2-pyridones and 4-amino-2-pyrones

At ambient temperature, triacetic acid lactone reacts with amines to produce 4-amino-2-pyrones. If the temperature is raised to 100 °C, 4-hydroxy-2-pyridones are generated.

Synthesis, CYP 450 evaluation, and docking simulation of novel 4-aminopyridine and coumarin derivatives

Four series of novel compounds based on 4-aminopyridine, glatiramer acetate, pyrone, and coumarin backbones were sufficiently synthesized and identified by spectroscopic methods. CYP enzyme inhibition assays of five predominate human P450 isozymes indicate that all compounds, except for 4-hydrazide pyridine 1c, seem to be less toxic than 4-aminopyridine. Further investigation of the compounds using molecular docking experiments revealed different, the same, or stronger binding modes for most of the synthesized compounds, with both polar and hydrophobic interactions with the 1WDA and 1J95 receptors compared to benzoyl l-arginine amide and 4-aminopyridine, respectively. These results introduce the synthesized compounds as K+ channel blockers that could be considered for in vivo CNS disease studies.

Palladium-Catalyzed Synthesis of Benzothiophenes via Cross-Dehydrogenative Coupling of 4-Arylthiocoumarins and Pyrones

Benzothiophenes represent a pivotal class of sulfur heterocycles and their synthesis has attracted significant attention to generate bioactive scaffolds. Herein, we report a convergent, atom- and step-economic method for the synthesis benzothiophenes by cross-dehydrogenative coupling (CDC) of 4-arylthiocoumarins in good to excellent yields. We further demonstrate cross-dehydrogenative coupling of 4-arylthio-2-pyrones to afford alternative substitution of benzothiophenes. The presence of a labile ester carbonyl moiety provides functional handle for further functionalization by coumarin deconstruction. Most crucially, the manuscript demonstrates that the use of readily accessible templated synthesis has a significant potential for the rapid assembly of sulfur heterocycles by dehydrogenative coupling mechanism.

Design, synthesis, and biological evaluation of novel 2H-pyran-2-one derivatives as potential HIV-1 reverse transcriptase inhibitors

In search for more effective drugs against HIV infection acting as non-nucleoside reverse transcriptase inhibitors (NNRTIs), a series of new molecules with hybrid structures based on the natural product (+)-calanolide A and the synthetic molecule α-APA, known as potent and selective inhibitors of this enzyme, were selected by docking calculations. A convergent synthetic strategy gave 21 compounds with a 2 H-pyran-2-one structural unit and bearing isosteric modifications, which were tested against HIV-infected CEM cell cultures. Only compound 6 (4-((2-(1H-indol-3-yl)ethyl)amino)-6-methyl-2H-pyran-2-one) displayed inhibitory activity (EC50: 25-50 μM). However, it was associated with a relatively high cytostatic effect on human T lymphocyte (CEM) cell cultures, not easily predictable, neither by the chemical structure nor by the computational approach. Although this drug design has failed in selecting a novel scaffold for NNRTIs, the results have driven the interest towards new potential antitumor molecules showing activity against L1210 murine leukemia and HeLa cervix carcinoma cells, among which compound 21 (6-methyl-4-((2-(naphthalen-1-yl)ethyl)sulfonyl)-2H-pyran-2-one) was the most effective (IC50: 0.95 and 2.9 μM, respectively).

N-heterocyclic carbene derived Nickel-Pincer complexes: Efficient and applicable catalysts for Suzuki-Miyaura coupling reactions of aryl/alkenyl tosylates and mesylates

Catalytic activities of NHC-derived nickel-pincer complexes for the Suzuki-Miyaura coupling reactions of aryl/alkenyl to- sylates and mesylates are described. In the presence of a catalytic amount of nickelacycle 1a, a wide array of tosylates and mesylates reacted with several aryl- and alkenylboronic acids to afford the coupling products, generally in high yields. Fine tuning of the reaction conditions for each class of electrophiles was achieved only by choosing the appropriate reaction medium (DME for tosylates, dioxane for mesylates).

Regioselective synthesis of pyrone-annulated sulfur heterocycles by aryl radical cyclization

The tri-n-butyltin hydride mediated cyclization of a number of 4-(2′-bromophenoxymethyl)-7-methylthiopyrano[3,2-c]pyran-5-ones have been carried out to afford tetracyclic [6,6]pyranothiopyrans in 70-80% yield and good to excellent diastereoselectivity. Th

Regioselective heck couplings of α,β-unsaturated tosylates and mesylates with electron-rich olefins

(Chemical Equation Presented) Highly regioselective Heck couplings of α,β-unsaturated tosylate and mesylate derivatives with N-acyl N-vinylamines and vinyl ethers were achieved. Several 2-alkoxy-1,3-dienes and 2-acylamino-1,3-butadienes were synthesized i

Halogenated-2-pyrones in Sonogashira cross-coupling: limitations, optimisation and consequences for GC analysis of Pd-mediated reactions

The Sonogashira couplings of 4-bromo-6-methyl-2-pyrone (5) with phenylacetylene, mediated by Pd(PPh3)2Cl2 in the presence of a CuI co-catalyst, have been investigated in detail. The concentration of Pd dramatically influences the product yield, with lower Pd-loadings favouring higher conversions and purer cross-coupled product. A post reaction time-dependence in product conversion is seen in samples quenched solely on silica-gel (eluted with CH2Cl2). The effect is mirrored in reactions employing 4-nitro-bromobenzene (14) and to a lesser extent (E) and (Z)-ethyl 3-iodo-2-propenonate (16) under similar conditions. A more efficient quenching system (using excess dppe) has been developed to enable accurate determinations in product conversions. Alternatively, solvent and base (Et3N) removal in vacuo, or quench with saturated aqueous ammonium chloride, prevents further turnover in Sonogashira coupling. An ESI-MS study on samples eluted through silica was undertaken to probe the nature of the soluble Pd/Cu species. The Sonogashira cross-coupling of 4-chloro- and 6-chloro-2-pyrone (18 and 20, respectively) has further been investigated. The former undergoes successful coupling, however the latter decomposes in polar aprotic and protic solvents under standard conditions, through a chlorine substitution process, making Pd-mediated reactions problematic.

Efficient route to 4-substituted-2(5H)-furanones, 2(1H)-quinolones, and pyrones by nickel-catalyzed cross-coupling of arenesulfonates with organozinc reagents

Nickel(II)-catalyzed cross-coupling reactions of 4-tosyl-2(1H)-quinolone, pyrone, and 2(5H)-furanone with various organozinc reagents provide an efficient and practical method for the high-yielding synthesis of 4-substituted 2(1H)-quinolones, pyrones, and 2(5H)-furanones. Copyright

Sonogashira cross-coupling reactions catalysed by copper-free palladium zeolites

A heterogeneous copper-free [Pd(NH3)4]2+/ (NH4)Y catalyst was employed to achieve the heterogeneous Sonogashira reaction of aryl halides with terminal alkynes. Several reaction parameters like solvent, base and temperature were evaluated. When optimised, the coupling reaction of bromobenzene with phenylacetylene gave a 45% yield of diphenylacetylene within 3 h using only 1 mol % Pd. This catalyst was successfully applied to the coupling reaction of a range of aryl iodides and bromides: aryl iodides and activated aryl bromides gave almost quantitative yields and non-activated aryl bromides led to reasonable yields (20% to 45%). This heterogeneous [Pd(NH3)4]2+/(NH 4)Y catalyst was shown to be efficient, stable towards leaching and recyclable for the copper-free Sonogashira reaction.