6533b823fe1ef96bd127dfce

RESEARCH PRODUCT

ChemInform Abstract: Carbazole Synthesis via an in situ Trapping Strategy with Indolyl Enol Ethers.

Carsten RehnBeate PeschelUlf PindurWerner MassaM. Rogge

subject

Dimethyl acetylenedicarboxylatechemistry.chemical_compoundAtropisomerChemistryCarbazoleAlkoxy groupGeneral MedicineRing (chemistry)EnolMedicinal chemistryAdductSodium hydride

description

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

yearjournalcountryeditionlanguage
2010-08-18ChemInform
https://doi.org/10.1002/chin.199513145