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Lithium Tetrafluoroborate-assisted Reactions Of N-(.alpha.-aminoalkyl)benzotriazoles With Olefins And 1,3-dienes. New Syntheses Of 1,2,5,6-tetrahydropyridinium Salts, 1,2,3,4-tetrahydroquinolines, And Some Related Heterocyclic Systems

A. R. Katritzky, M. F. Gordeev
Published 1993 · Chemistry

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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



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