. alpha.-Lithiation of N-alkylcarbazoles: preparation of N-(E)-styrylcarbazole

AR Katritzky, F Saczewski…

文献索引：Katritzky, Alan R.; Saczewski, Franciszek; Marson, Charles M. Journal of Organic Chemistry, 1985 , vol. 50, # 9 p. 1351 - 1355

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被引用次数: 19

摘要

Alkylation of carbazole with [(chloromethyl) thio] benzene gave the key intermediate N- [(phenylthio)-methyllcarbazole (2). Treatment of 2 with n-butyllithium at low temperature gave an a-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)- ...