Regioselective Fischer Indole Route to 3-Unsubstituted Indoles

Dalian Zhao, David L. Hughes, Dean R. Bender, Anthony M. DeMarco, Paul J. Reider

Research output: Contribution to journalArticlepeer-review

43 Scopus citations

Abstract

Use of Eaton's reagent (P2O5/MeSO3H) as acid catalyst in the Fischer indole reaction using methyl ketones provides unprecedented regiocontrol to form the 3-unsubstituted indoles. In several instances where the harshness of the reagent causes decomposition and low yields, dilution in sulfolane or dichloromethane results in far less degradation and higher yields of indoles. Steric effects and the acidity of the medium are the two major factors that control the regioselectivity. The role of the P2O5 in the reagent mixture P2O5/MeSO3H is simply as a drying agent when used as catalyst for the Fischer indole reaction.

Original languageEnglish (US)
Pages (from-to)3001-3006
Number of pages6
JournalJournal of Organic Chemistry
Volume56
Issue number9
DOIs
StatePublished - Apr 1 1991
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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