Pure Appl. Chem., 2003, Vol. 75, No. 10, pp. 1417-1432
doi:10.1351/pac200375101417
Novel chemistry of indole in the synthesis of heterocycles*
G.W. Gribble
Department of Chemistry, Dartmouth College, Hanover, NH 03755, USA
Abstract:
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.
*Lecture presented at the 4th Florida Heterocyclic Conference, Gainesville, Florida, 10-12 March 2003. Other presentations are published in this issue, pp. 1403-1475.
All articles from the 4th Florida Heterocyclic Conference, Gainesville, Florida, USA, 10–12 March 2003.