287487-29-0Relevant academic research and scientific papers
E/Z(C=C)-Isomerization of enamines of 3-formyl-4-hydroxycoumarin induced by organic solvents
Traven,Ivanov,Lebedev,Chibisova,Milevskii,Solov'Eva,Polshakov,Alexandrov,Kazheva,Dyachenko
experimental part, p. 1605 - 1611 (2011/05/04)
According to 1H and 13C NMR data, enamines of 3-formyl-4-hydroxycoumarin exist in the keto enamine tautomeric form and undergo Z/E-isomerization around the C=C bond in CDCl3, DMSO-d6, and CD3OD at room temperature. The activation energies of E/Z-isomerization were measured experimentally and calculated by the B3LYP/6-311++G(d,p) method. An X-ray diffraction study showed that 3-(benzyliminomethyl)chromane-2,4-dione in the crystalline state exists as a mixture of two keto enamine isomers.
Rapid microwave-assisted solution phase synthesis of substituted 2-pyridone libraries
Gorobets, Nikolay Yu.,Yousefi, Behrooz H.,Belaj, Ferdinand,Kappe, C. Oliver
, p. 8633 - 8644 (2007/10/03)
2-Pyridone and 2-quinolone analogues are well-known biologically active heterocyclic scaffolds. Libraries of 3,5,6-substituted 2-pyridone derivatives are generated by rapid microwave assisted solution phase methods using a one-pot, two-step protocol. The three-component condensation of CH-acidic carbonyl compounds, N,N-dimethylformamide dimethylacetal and methylene active nitriles, leads to 2-pyridones and fused analogues in moderate to good overall yields and high purities. The proposed mechanism of this novel multi-component reaction, structure elucidation of products and intermediates are discussed.
