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Synthesis 2000; 2000(8): 1081-1083
DOI: 10.1055/s-2000-6329
short paper
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Regiocontrolled Annellation Reactions Starting from Diethoxymethyl Protected Indole

Johannes Kraxner* , Peter Gmeiner
  • *Department of Medicinal Chemistry, Emil Fischer Center, Friedrich-Alexander University, Schuhstraße 19, D-91052 Erlangen, Germany; Fax +49 (91 31) 8 52 25 85; E-mail: gmeiner@pharmazie.uni-erlangen.de
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Publikationsdatum:
31. Dezember 2000 (online)

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Directed metallation of the diethoxymethyl protected indole 4 followed by treatment with β-nitrostyrene leads to the 1,2-disubstituted indole 5. Using 5 as a central intermediate, the tricyclic annellation products of type 2 and 3 were accessed when the regiochemical outcome of the reactions could be controlled.

indoles - metallation - rearrangements