Journal of Organic Chemistry p. 1351 - 1355 (1985)
Update date:2022-07-29
Topics:
Katritzky, Alan R.
Saczewski, Franciszek
Marson, Charles M.
Alkylation of carbazole with <(chloromethyl)thio>benzene gave the key intermediate N-<(phenylthio)methyl>carbazole (2).Treatment of 2 with n-butyllithium at low temperature gave an α-lithio derivative 3, which reacted with a variety of electrophiles, affording N-<(phenylthio)alkyl>carbazoles 4a-g.Removal of the activating phenylthio group in 4a-g was achieved by Raney nickel desulfurization.Three successful routes to the novel N-(E)-styrylcarbazole (10) are described. 1H NMR and 13C NMR assignments of N-alkylcarbazoles are discussed.
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(1985)
