Carbazole synthesis via an in situ trapping strategy with indolyl enol ethers

U Pindur, M Rogge, C Rehn, W Massa…

Index: Pindur, Ulf; Rogge, Martina; Rehn, Carsten; Massa, Werner; Peschel, Beate Journal of Heterocyclic Chemistry, 1994 , vol. 31, # 4 p. 981 - 988

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Citation Number: 7

Abstract

Abstract Indolyl enol ethers, generated from the alkoxy (indolyl) carbenium tetrafluoroborates 1 by treatment with sodium hydride, can be trapped with dimethyl acetylenedicarboxylate or N-phenylmaleimide to furnish the selectively functionalized carbazoles 3, 4, 5, 9, 10, and 13. In addition, the biaryl derivatives 6 and 11 are produced by a ring-opening reaction of the primarily formed Diels-Alder adduct. In the case of the biaryl ...