0000000000013708
AUTHOR
M. Rogge
showing 7 related works from this author
[a]-Anellated carbazoles with antitumor activity: Synthesis and cytotoxicity
1996
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
1991
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.
2010
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
1995
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.
2010
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
1994
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.
2010
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.