Premium
Carbazole synthesis via an in situ trapping strategy with indolyl enol ethers
Author(s) -
Pindur Ulf,
Rogge Martina,
Rehn Carsten,
Massa Werner,
Peschel Beate
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310448
Subject(s) - chemistry , carbazole , adduct , dimethyl acetylenedicarboxylate , sodium hydride , enol , derivative (finance) , hydride , ring (chemistry) , alkoxy group , organic chemistry , catalysis , cycloaddition , hydrogen , alkyl , financial economics , economics
Indolyl enol ethers, generated from the alkoxy(indolyl)carbenium tetrafluoroborates 1 by treatment with sodium hydride, can be trapped with dimethyl acetylenedicarboxylate or N‐phenylmaleimide to furnish the selectively 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.