Premium
Intramolecular Fischer Indole Synthesis and its Combination with an Aromatic [3,3]‐Sigmatropic Rearrangement for the Preparation of Tricyclic Benzo[ cd ]indoles
Author(s) -
Park InKeol,
Park Jun,
Cho CheonGyu
Publication year - 2012
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201108970
Subject(s) - intramolecular force , sigmatropic reaction , chemistry , tricyclic , indole test , tandem , aryl , ring (chemistry) , stereochemistry , medicinal chemistry , organic chemistry , alkyl , materials science , composite material
At the end of the tether : Aryl hydrazides that have carbonyl groups tethered at the para position of the aromatic ring undergo an intramolecular Fischer indolization reaction to give the corresponding indolophanes. Strategic insertion of a double bond in the tether enables a tandem aromatic [3,3] sigmatropic rearrangement reaction to occur to give tricyclic benzo[ cd ]indoles.