6533b85afe1ef96bd12b89d7
RESEARCH PRODUCT
Carbazole synthesisviaanin situtrapping strategy with indolyl enol ethers
Werner MassaUlf PindurBeate PeschelCarsten RehnM. Roggesubject
chemistry.chemical_classificationDimethyl acetylenedicarboxylateAtropisomerCarbazoleOrganic ChemistryEnolMedicinal chemistryAdductSodium hydridechemistry.chemical_compoundchemistryEnol etherAlkoxy groupOrganic chemistrydescription
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
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1994-07-01 | Journal of Heterocyclic Chemistry |