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In-Keol Park, Jun Park and Prof. Cheon-Gyu Cho Intramolecular Fischer Indole Synthesis and its Combination with an Aromatic [3,3]-Sigmatropic Rearrangement for the Preparation of Tricyclic Benzo[cd]indoles Angewandte Chemie International Edition 51

Version of Record online: 19 JAN 2012 | DOI: 10.1002/anie.201108970

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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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