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Synthesis of Benzo[ a ]carbazoles from 2‐Arylindoles via a Sequential Propargylation, Propargyl‐Allenyl Isomerization, and 6π‐Electrocyclization
Author(s) -
Lim Jin Woo,
Kim Se Hee,
Kim Jimin,
Kim Jae Nyoung
Publication year - 2015
Publication title -
bulletin of the korean chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.237
H-Index - 59
ISSN - 1229-5949
DOI - 10.1002/bkcs.10258
Subject(s) - isomerization , propargyl , chemistry , benzene , catalysis , medicinal chemistry , combinatorial chemistry , organic chemistry
An efficient two-step synthetic approach of benzo[a]carbazoles from 2-arylindoles has been developed. The first step is a propargylation of 2-arylindoles at the 3-position catalyzed by montmorillonite K-10 in benzene. The second step is 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)-catalyzed sequential propargyl-allenyl isomerization and a concomitant 6π-electrocyclization process involving two aromatic π-bonds.