I  U  P  A  C

 

 

 

News & Notices

Organizations & People

Standing Committees

Divisions

Projects

Reports

Publications
. . CI
. . PAC
. . Macro. Symp.

. . Books
. . Solubility Data

Symposia

AMP

Links of Interest

Search the Site

Home Page

 

Pure Appl. Chem. 75(10), 1417-1432, 2003

Pure and Applied Chemistry

Vol. 75, Issue 10

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.


Page last modified 30 September 2003.
Copyright © 2003 International Union of Pure and Applied Chemistry.
Questions or comments about IUPAC, please contact, the Secretariat.
Questions regarding the website, please contact web manager.