95249-52-8Relevant academic research and scientific papers
New synthesis of amines and amides mediated by additions of benzotriazole to enamines and enamides and transformations of the adducts
Katritzky,Jurczyk,Rachwal,Rachwal,Shcherbakova,Yannakopoulou
, p. 1295 - 1298 (2007/10/02)
Adducts of type N - C - Bt can be obtained in which the nitrogen atom is derived from an N-vinyl non-basic heterocyclic NH compound or a secondary amide, or in which the central carbon is derived from a ketone by the addition of benzotriazole to an enamine or enamide. Thus, 9-vinylcarbazole, 1-vinylpyrrolidin-2-one and 1-(1-ethylprop-1-enyl)pyrrolidine afforded the corresponding N-(1-benzotriazolylalkyl)-substituted compounds which could be alkylated by various methods in good yield. The range of benzotriazole mediated syntheses of amines and amides is significantly extended in this way.
α-Lithiation of N-Alkylcarbazoles: Preparation of N-(E)-Styrylcarbazole
Katritzky, Alan R.,Saczewski, Franciszek,Marson, Charles M.
, p. 1351 - 1355 (2007/10/02)
Alkylation of carbazole with benzene gave the key intermediate N-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-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.
