0000000000013708
AUTHOR
M. Rogge
[a]-Anellated carbazoles with antitumor activity: Synthesis and cytotoxicity
The cycloadducts3,5, and7, readily available from methoxy-substituted 3-vinylindoles1 and2, were dehydrogenated withDDQ to the coplanar [a]-anellated carbazoles4,6, and8. Compound4a, also characterized by X-ray structural analysis, shows significant cytotoxicity against K562 und RXF393 human tumor cell lines.
Diels-Alder-Reaktionen von Vinylindolen mit Arin und 1,4-Benzochinonen: Neue potentielle DNA-Interkalatoren
Diels-Alder reactions of 2- and 3-vinylindoles with aryne, 1,4-benzo- and 1,4-naphtho-quinone lead to new six-ring annellated carbazoles. Molecular modeling studies predict that the compounds with coplanar framework are able to intercalate with the B-DNA.
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
First synthesis of chiral 3-vinylindoles as 4π-components for diels-alder reactions
The first syntheses of chiral 3- and 2-vinylindoles bearing sulfoxide or (-)-menthyloxy functional groups at the β-vinyl positions by way of procedures based on the Horner-Wadsworth-Emmons and Wittig reactions, respectively, are described. Some Diels-Alder reactions demonstrating the 4π-reactivity of these compounds are reported.
ChemInform Abstract: (a)-Anellated Carbazoles with Antitumor Activity: Synthesis and Cytotoxicity.
The cycloadducts3,5, and7, readily available from methoxy-substituted 3-vinylindoles1 and2, were dehydrogenated withDDQ to the coplanar [a]-anellated carbazoles4,6, and8. Compound4a, also characterized by X-ray structural analysis, shows significant cytotoxicity against K562 und RXF393 human tumor cell lines.
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
ChemInform Abstract: First Synthesis of Chiral 3-Vinylindoles as 4π-Components for Diels- Alder Reactions.
The first syntheses of chiral 3- and 2-vinylindoles bearing sulfoxide or (-)-menthyloxy functional groups at the β-vinyl positions by way of procedures based on the Horner-Wadsworth-Emmons and Wittig reactions, respectively, are described. Some Diels-Alder reactions demonstrating the 4π-reactivity of these compounds are reported.