Use of Vinyl Sulfides in Fischer Indole Reactions

Abstract

Vinyl sulfides accessed via Wittig olefination with thioalkylphosphonium salts are used as aldehyde- or ketone surrogates in Fischer indole reactions. These vinyl sulfides react with arylhydrazines in the presence of TsOH·H₂O in refluxing ethanol or dichloroethane to yield diverse 3-substituted and 2,3-disubstituted indoles or azaindoles. The utility of this chemistry is highlighted with the efficient preparation of three biomedically relevant compounds: 4-aza-melatonin, a furoindoline, and an indomethacin-like CRTh2 antagonist.

Key words

vinyl sulfide - Wittig olefination - Fischer indole synthesis - azaindole - thioalkylphosphonium salts

Publication History

Received: 13 April 2022

Accepted after revision: 02 June 2022

Accepted Manuscript online:
02 June 2022

Article published online:
12 July 2022

• References

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