25105-60-6Relevant articles and documents
Synthesis of new biologically active isothiazolo[4,5-b]carbazole-type tetracyclic derivatives via an indole-2,3-quinodimethane approach
Miambo, Raimundo F.,Laronze-Cochard, Marie,Lawson, Ata-Martin,Guillot, Régis,Baldeyrou, Brigitte,Lansiaux, Amélie,Supuran, Claudiu T.,Sapi, Janos
, p. 8286 - 8302 (2014)
A number of isothiazolo[4,5-b]carbazole derivatives were prepared via a Diels-Alder approach involving thermally induced indole-2,3-quinodimethane intermediates. Preliminary biological tests revealed a GSK-3β kinase inhibitor (29) and some free NH group containing compounds (17d, 19c, 29) displayed selective human carbonic anhydrase I inhibitory activities.
Transimination reactions in [b-3C-im][NTf2] ionic liquid
Chen, Chao-Wen,Tseng, Ming-Chung,Hsiao, San-Kai,Chen, Wen-Hao,Chu, Yen-Ho
experimental part, p. 4188 - 4193 (2011/06/26)
Compared to conventional molecular solvents, the ionic liquid [b-3C-im][NTf2] was found to promote transimination reactions with up to ~100-fold rate enhancement. This rate effect observed at ambient temperature might be explained by the fact that the ionic liquid displays weak Lewis acidity with very low, if any, nucleophilicity and its imidazolium cation is expected to interact by associating with, and thus electrophilically activating, the CN bond of the starting imine, leading to increased stabilization of the polar, charged intermediate species and ultimately, rapid product formation. Moreover, the presence of 1 mol% Sc(OTf)3 in [b-3C-im][NTf2] further facilitates the transimination reactions studied.
Reactions of N-Chloro-N-alkylbenzylamines with Amines in Acetonitrile. Origin of Steric Effect in Imine-Forming Elimination
Cho, Bong Rae,Suh, Young Wook
, p. 2855 - 2858 (2007/10/02)
Reaction of N-chloro-N-alkylbenzylamines in which the alkyl group is Me, Et, i-Pr, sec-Bu, and t-Bu with MeNH2 and Et2NH in MeCN have been studied kinetically.The eliminations are quantitative and regiospecific, producing only N-benzylidenealkylamines.The relative rates of elimination for Me/Et/i-Pr/sec-Bu/t-Bu alkyl substituents are 1/0.6/0.4/0.3/0.1 with MeNH2 and 1/0.5/0.3/0.2/0.03 with Et2NH, respectively.Comparison with published data reveals that Charton's value for the imine-forming elimination decreases with the variation of the base-solvent from MeONa-MeOH to MeNH2-MeCN but increases when the base is changed from MeNH2 to Et2NH.For a given base, Hammett ρ and kH/kD values decrease and the ΔH(excit.) and ΔS(excit.) values increase with bulkier alkyl substituents.From these results, the origin of the steric effect in imine-forming elimination is attributed to the repulsive interaction between the alkyl group and the base in the transition state.