234774-85-7

Upstream product

• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 31913-41-4 6-methyl-4-tosyloxy-2(2H)-pyranone 
• 100-46-9 benzylamine 

Downstream Products

• 234774-83-5 C₁₀H₁₀O₂CH₂NC₇H₇C₃H₄ 
• 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 
• 1434146-82-3 N-benzyl-N-(6-methyl-2-oxo-2H-pyran-4-yl)propionamide 
• 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 
• 934296-35-2 5-benzyl-3-methyl-5,5a,6,7,8,9-hexahydro-pyrano[4,3-b]quinolin-1-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.

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).

A study on the regioselectivity in N,C-acylation of β-enamino-esters

With the aim to produce the new corresponding amide, amino pyrone 1 [=4-(benzylamino)-6-methyl-2H-pyran-2-one] was acylated in dichloromethane in the presence of triethylamine, obtaining an unexpected mixture of N- and C-acyl products in a 60:40 ratio, respectively. The regioselective investigation was enlarged by using a series of organic bases and taking into account both solvent effects and acyl halide structure. Conditions able to give pure amides or pure C-acyl products were established. The study also includes the reactivity of a β-enamino-ester with NH group involved in an intramolecular hydrogen bond, where pure C-acyl products were obtained.