0000000000522717
AUTHOR
Beate Peschel
ChemInform Abstract: Carbazole Synthesis via an in situ Trapping Strategy with Indolyl Enol Ethers.
Indolyl enol ethers, generated from the alkoxy(indolyl)carbenium tetra- fluoroborates (1) by treatment with sodium hydride, can be trapped with dimethyl acetylenedicarboxylate or N-phenylmaleimide to furnish the se- lectively 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 derivative (6), an X-ray crystal structure analysis yields valuable information on constitutions and configurations in the biaryl series. The phenomenon of atropisomerism is discussed for this compound
Carbazole synthesisviaanin situtrapping strategy with indolyl enol ethers
Indolyl enol ethers, generated from the alkoxy(indolyl)carbenium tetra- fluoroborates (1) by treatment with sodium hydride, can be trapped with dimethyl acetylenedicarboxylate or N-phenylmaleimide to furnish the se- lectively 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 derivative (6), an X-ray crystal structure analysis yields valuable information on constitutions and configurations in the biaryl series. The phenomenon of atropisomerism is discussed for this compound