15113-00-5Relevant articles and documents
Photoelectron spectroscopy of quinoline derivatives. Correlation of experimental ionization potentials with calculated molecular energies
Ahmed,Julliard,Chanon,Chanon,Gracian,Pfister-Guillouzo
, p. 335 - 343 (1997)
Experimental ionization potentials of quinoline 1 and substituted quinolines: 6-methylquinoline 2, 2,6-dimethylquinoline 3, 6-methoxyquinoline 4, 3-bromoquinoline 5, 2-chloro-4-methylquinoline 6, 4-hydroxyquinoline 7, 4-hydroxy-2-methylquinoline 8, 2-hydroxy-4-methylquinoline 9, 4-methoxyquinoline 10, 4- methoxy-2-methylquinoline 11, 2-methoxy-4-methylquinoline 12, were measured by photoelectron spectroscopy. Molecular orbital energies of the same derivatives were calculated by the Austin Method 1. The assignments of the bands of the photoelectron spectra were done with the aid of the theoretical calculations and on the basis of the substituent effects. For quinolines 1-6 a good agreement was found between the experimental ionization potentials and the calculated orbital energies.
Silver-catalyzed oxidative coupling of aniline and ene carbonyl/acetylenic carbonyl compounds: An efficient route for the synthesis of quinolines
Zhang, Xu,Xu, Xuefeng
supporting information, p. 3089 - 3093 (2015/02/19)
An efficient silver-mediated coupling of aniline with ene carbonyl/acetylenic carbonyl compounds for the synthesis of quinolines is reported. The transformation is effective for a broad range of substrates, thus enabling the expansion of substituent architectures on the heterocyclic framework. The electronic properties of the substituents on the amine have been investigated. It was found that molecules with both electron-donating and electron-withdrawing substituents were suitable substrates for this transformation, and the expected products were obtained in moderate to excellent yields. The use of a single catalytic system to mediate chemical transformations in a synthetic operation is important for the development of new atom-economic strategies and this strategy is efficient in building complex structures from simple starting materials in an environmentally benign fashion.
On the thermally induced rearrangement of 2-alkoxypyridines to N-alkylpyridones
Lister, Troy,Prager, Rolf H.,Tsaconas, Michael,Wilkinson, Kerry L.
, p. 913 - 916 (2007/10/03)
Analogues of 2-methoxypyridine undergo rearrangement to N-methylpyridones under flash vacuum pyrolysis (FVP) conditions. Ethoxy derivatives undergo competitive ethyl migration and elimination of ethylene. Analogues of 4-methoxypyridine do not undergo rearrangement under FVP conditions, but demethylation on silica may occur. The ease of rearrangement follows the basicity of the alkoxyhetarene to some extent. The vapour-phase rearrangements have been contrasted to condensed-phase pyrolyses. and a four-centre transition state for the former is supported by computation. The rearrangement allows structural assignment to the two products from the reaction of 2,4-dichloroquinoline with pyrrolidine.
