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Polycyclic Indoline Derivatives by Dearomatizing Anionic Cyclization of Indole and Tryptamine-Derived Ureas
Jessica E Hill1, Quentin Lefebvre1, Laura A Fraser1
1School of Chemistry , University of Bristol , Cantock's Close , Bristol BS8 1TS , U.K.
Abstract:
The base-promoted dearomatizing cyclization of anionic indole-containing urea derivatives provided tri- or tetracyclic indoline-containing scaffolds from lithiated urea intermediates. 3-Substituted indoles, including tryptamine derivatives, generally underwent the reaction in high yield and with excellent diastereoselectivity. In situ IR spectroscopy suggests a deprotonation-carbolithiation-reprotonation mechanism.
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