341027-36-9Relevant academic research and scientific papers
Improved procedure for the enantioselective synthesis of dihydrooxazolo and dihydrothiazolo ring-fused 2-pyridones
Chorell, Erik,Edvinsson, Sofie,Almqvist, Fredrik
supporting information; experimental part, p. 2461 - 2463 (2010/07/04)
Improved procedures to synthesize enantioselectively analogues of a peptidomimetic scaffold with high biological relevance have been developed. Experimental design led to a general method for the preparation of dihydrooxazolo ring-fused 2-pyridones in good yields and high enantiomeric purity. The knowledge gained from this was also used to improve the microwave-accelerated synthesis of dihydrothiazolo ring-fused 2-pyridones to give complete stereo retention and high yields.
Regioselective halogenations and subsequent Suzuki-Miyaura coupling onto bicyclic 2-pyridones
Bengtsson, Christoffer,Almqvist, Fredrik
supporting information; experimental part, p. 972 - 975 (2010/04/30)
(Chemical Equation Presented) A selective synthesis of 6-bromo-8-iodo dihydro thiazolo ring-fused 2-pyridones is described. These halogenated 2-pyridones are selectively arylated by sequential Suzuki - Miyaura couplings. This approach can advantageously be used to synthesize focused libraries of substituted ring-fused 2-pyridones, a class of compounds with novel antibacterial properties.
Microwave-assisted decarboxylation of bicyclic 2-pyridone scaffolds and identification of Aβ-peptide aggregation inhibitors
Aberg, Veronica,Norman, Fredrik,Chorell, Erik,Westermark, Andreas,Olofsson, Anders,Elisabeth Sauer-Eriksson,Almqvist, Fredrik
, p. 2817 - 2823 (2007/10/03)
A reagent-free microwave-assisted decarboxylation procedure for carboxylic acid functionalized bicyclic 2-pyridones has been developed. This new method, based on microwave heating at 220°C for 600 seconds in N-methyl pyrrolidone (NMP), proved to be practical and very efficient, resulting in decarboxylated 2-pyridones in near-quantitative yields. The decarboxylated products and the intermediate 2-pyridones in the form of carboxylic acid methyl esters and carboxylic acids were screened for their effect on Aβ-peptide aggregation. Two out of the 21 2-pyridones described in this study inhibited amyloid formation of the Alzheimer Aβ(1-40) peptide. The effect was seen even at a 4: 1 ratio of 2-pyridone and monomeric Aβ-peptide. The Royal Society of Chemistry 2005.
An enantioselective ketene-imine cycloaddition method for synthesis of substituted ring-fused 2-pyridinones
Emtenaes,Alderin,Almqvist
, p. 6756 - 6761 (2007/10/03)
Previously, a method for the stereoselective synthesis of β-lactams, starting from 2H-δ2-thiazolines and Meldrum's acid derivatives, has been reported from our laboratory. We now report a new method for the synthesis of optically active, highly substituted ring-fused 2-pyridinones. This was discovered when 2-alkyl-δ2-thiazolines and Meldrum's acid derivatives were treated with HCl(g) in benzene at 5 → 78 °C. Further refinement of the synthetic protocol revealed that use of 1,2-dichloroethane as solvent at 0 → 64 °C led to the desired 2-pyridinones in good yields and with excellent enantioselectivity. Use of these conditions allowed preparation of 2-pyridinones from several different δ2-thiazolines and Meldrum's acid derivatives and may be a general route to 2-pyridinones.
