Formation Of 2-pyridones Research Articles

Photocatalyst-Free Singlet Oxygen-Induced Oxygenation: AStrategy for the Preparation of 5-Cyano-2-pyridones Driven by Blue-Light Irradiation.

A mild, catalyst- and metal-free photochemical protocol for the oxygenation of 3-cyano-1,4-dihydropyridines to 5-cyano-2-pyridones was developed. Utilizing molecular oxygen from the air as the oxidant and a cheap blue LED lamp as the light source, a variety of 3-cyano-1,4-dihydropyridines were converted into the corresponding 5-cyano-2-pyridones in moderate to excellent yields. Exploration of the substrate scope revealed that 3-cyano and 4-aryl groups play an important role in the formation of 2-pyridone.

Iodine catalyzed simple and efficient synthesis of antiproliferative 2-pyridones

A simple and efficient method for the selective synthesis of 2-pyrdones from 4H-pyrans using iodine as catalyst and ethanol as solvent was developed. The present method is equally effective for both aromatic and hetero aromatic ring containing 4H-pyrans. The compatibility with various functional groups, mild reaction conditions, high yields and application of inexpensive, readily and easily available iodine as catalyst and formation of 2-pyridones as major products are the advantages of the present procedure. In vitro antiproliferative activity of the final synthesized compounds was evaluated with four different human cancer cell lines (Lung adenocarcinoma-A549, Hepatocarcinoma-HepG2, Breast carcinoma-MCF-7 and Ovarian carcinoma-SKOV3) and normal human lung fibroblast cell line (MRC-5). Compounds 2b showed better inhibition against MCF-7, HepG2 and A549 cell lines (IC50 8.00±0.11, 11.93±0.01 and 15.85±0.04μM, respectively) as compared with doxorubicin and also 2e showed moderate inhibition against MCF-7, HepG2 (IC50 9.32±0.21 and 20.22±0.01μM, respectively, cell lines, respectively) as compared with doxorubicin. As many clinically used antiproliferative agents induce apoptosis in cancer cells hence, the 2-pyridone analogues were also tested for their ability to induce apoptosis in MCF-7 cells using the caspases-3 and -9 assays.

Rhodium-Catalyzed Enantioselective Cycloaddition Route to Indolizidines

Described herein is a synthesis of indolizidines by an asymmetric Rh(I)-catalyzed [2+2+2] cycloaddition of 1,1-disubstituted alkenyl isocyanates to terminal alkynes. The reaction proceeds in moderate to high yields with a high level of enantio- and regioselectivity in the presence of the phosphoramidite ligands. Aliphatic alkynes gave lactams A as major products whereas vinylogous amides B predominated with aryl alkynes. The formation of 2-pyridones E as the major byproduct was suppressed under high dilution reaction conditions (typically 0.04 M). The isolated yields were low with sterically demanding substituents (e.g., R1 = i-Pr, Cy) and in such reactions an increase in the 2-pyridone byproduct was observed, presumably due to a slow rate of coordination-insertion of the alkene with Rh.

N-3-oxoalkylamides and -thioamides in the synthesis of heterocyclic compounds. 7*. Study of the cyclization of N-(3-oxoalkyl)-amides of tosylacetic acid

Alkyl-substituted N-(3-oxoalkyl)amides of tosylacetic acid are cyclized under the action of bases with the formation of 3-tosyl-3,6-dihydropyridin-2(1H)-ones. In the presence of a phenyl substituent at position C(1) of the 3-oxoalkyl chain the reaction proceeds with the formation of 2-pyridones. The principles influencing the regiodirection of cyclization are explained.

ChemInform Abstract: Formation of 2-Pyridone in the Process of the Enamine Rearrangement of Pyrimidinium Salts.

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Formation of 2-pyridone in the process of the enamine rearrangement of pyrimidinium salts

Formation of 2-pyridone in the process of the enamine rearrangement of pyrimidinium salts