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Ynone Promoted Deaminative Coupling of Gramines with C- and N-Nucleophiles
Iker Hernández1, Guillermo Domínguez1, Vadim A Soloshonok1
1Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Manuel Lardizabal Pasealekua 3, 20018 Donostia/San Sebastián, Spain.
Abstract:
The deaminative coupling of gramines with nucleophiles represents a versatile approach for structure diversification, but often involves non innocent conditions and/or reagents. Here a new acetylenic reagent 2 is developed for the C-N bond activation of gramines and their in situ coupling with C- and N-centered nucleophiles. Using the new acid/base- and redox-neutral ynone reagent 2 the coupling reactions proceed exceedingly as exemplified by the synthesis of several indol-3-ylmethyl derivatives, including new indole-benzodiazepine and indole-hydrazone conjugates.
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