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Publicly Available Published by De Gruyter January 1, 2009

Novel chemistry of indole in the synthesis of heterocycles

  • G. W. Gribble

Indoles that are substituted at the 2- or 3-position with electron-withdrawing groups (nitro, phenylsulfonyl) undergo nucleophilic addition, 1,3-dipolar cycloaddition, and Diels–Alder reactions to give a variety of indoles, pyrroloindoles, and carbazoles. New methods for the synthesis of furo[3,4-b]indoles and the novel ring system furo[3,4-b]pyrrole are described for the first time. Diels–Alder reactions of furo[3,4-b]pyrroles afford indoles after dehydration of the primary cycloadducts. Efficient syntheses of both 2- and 3-nitroindoles from indole are reported, and the first generation and successful electrophilic trapping of a 2,3-dilithioindole has been achieved.


Conference

Florida Heterocyclic Conference, Florida Heterocyclic Conference, FloHet, Florida Heterocyclic Conference, 4th, Gainesville, Florida, USA, 2003-03-10–2003-03-12


Online erschienen: 2009-1-1
Erschienen im Druck: 2003-1-1

© 2013 Walter de Gruyter GmbH, Berlin/Boston

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