Intramolecular Fischer Indole Synthesis and its Combination with an Aromatic [3,3]‐Sigmatropic Rearrangement for the Preparation of Tricyclic Benzo[ cd ]indoles | Zendy

Park InKeol | Zendy; Park Jun | Zendy; Cho CheonGyu | Zendy

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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.

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