17118-97-7Relevant academic research and scientific papers
Modeling the reactions of 1-naphthylamine and 4-methylaniline with humic acids: Spectroscopic investigations of the covalent linkages
Ononye,Graveel
, p. 537 - 541 (1994)
The covalent binding of two aromatic amines, 1-naphthylamine and 4- methylaniline, to substituted quinones in aqueous solutions has been studied as a model for the covalent binding of amines to humic acids. An imine compound was the only type of product identified for the reactions between 1- naphthylamine and selected quinones. Reactions of 4-methylaniline with the same quinones gave a 1,4- addition product in addition to the imine compound, although only the imine product was formed when the quinone had bulky substituents at the 2- and 6- positions. These results provide additional insight into the reactions of aromatic amines with humic acid quinones. The covalent binding of two aromatic amines, 1-naphthylamine and 4-methylaniline, to substituted quinones in aqueous solutions has been studied as a model for the covalent binding of amines to humic acids. An imine compound was the only type of product identified for the reactions between 1-naphthylamine and selected quinones. Reactions of 4-methylaniline with the same quinones gave a 1.4- addition product in addition to the imine compound, although only the imine product was formed when the quinone had bulky substituents at the 2- and 6- positions. These results provide additional insight into the reactions of aromatic amines with humic acid quinones.
Exploiting Iminoquinones as Electrophilic at Nitrogen "n+" Synthons for C-N Bond Construction
Mori-Quiroz, Luis M.,Comadoll, Chelsea G.,Super, Jonathan E.,Clift, Michael D.
supporting information, p. 7008 - 7013 (2021/09/18)
New methods for C-N bond construction exploiting the N-centered electrophilic character of iminoquinones are reported. Iminoquinones, generated in situ via the condensation of o-vinylanilines with benzoquinones, undergo acid-catalyzed cyclization to afford N-arylindoles in excellent yields. Under similar reaction conditions, homoallylic amines react analogously to afford N-arylpyrroles. Additionally, organometallic nucleophiles are shown to add to the nitrogen atom of N-alkyliminoquinones to provide amine products. Finally, iminoquinones are shown to be competent electrophiles for copper-catalyzed hydroamination.
