A. Katritzky, M. Gordeev
Jul 1, 1993
Citations
0
Influential Citations
29
Citations
Journal
Journal of Organic Chemistry
Abstract
Lithium tetrafluoroborate efficiently assists the ionization of N-(α-aminoalkyl)benzotriazoles in tetrahydrofuran solution to generate reactive iminium intermediates, which can be trapped with electron-rich olefins and with 1,3-dienes. Hetero Diels-Alder cycloadditions of N-(α-dialkylaminoalkyl)benzotriazoles and lithium tetrafluoroborate with 1,3-dienes thus gave 1,2,5,6-tetrahydropyridinium salts, while reactions of N-[α-(arylamino)alkyl]benzotriazoles with olefins and 1,3-dienes afforded substituted 1,2,3,4-tetrahydroquinolines, as well as examples of the new heterocyclic systems indeno[2,1-c]quinoline and pyrido[3,2,1-kl]-1,4-phenothiazine