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Pure Appl. Chem.
75(10), 1417-1432, 2003
Pure and Applied Chemistry
Vol. 75, Issue 10
Novel chemistry of indole in the synthesis of
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.
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