17972-12-2Relevant articles and documents
Synthesis of fluorinated pyrimidinones
Kosobokov, Mikhail D.,Struchkova, Marina I.,Arkhipov, Dmitry E.,Korlyukov, Alexander A.,Dilman, Alexander D.
, p. 73 - 79 (2013)
A method for the construction of fluorinated pyrimidinones based on the reaction of cyanodifluoromethyl- substituted amines with isocyanates is described. The use of ortho-iodophenylisocyanate in this reaction followed by copper catalyzed intramolecular amination affords fluorinated fused heterocycles - 4-fluoropyrimido[1,6-a]benzimidazol-1(2H)-ones.
Synthesis of 2-alkyl-1-aryl-1,2-dihydrochromeno[2,3-c]pyrrole-3,9-dione derivatives
Vydzhak,Panchishin, S. Ya.
experimental part, p. 2391 - 2397 (2009/05/30)
A preparative procedure for the synthesis of 2-alkyl-1-aryl-1,2- dihydrochromeno[2,3-c]pyrrole-3,9-diones from methyl 4-(o-hydroxyphenyl)-2,4- dioxobutanoate, aromatic aldehyde, and aliphatic amine is described.
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.