Use of Vinyl Sulfides in Fischer Indole Reactions

Parul Pal, Meghan Fragis, Srinivas Dharavath, Jarrod W. Johnson, Jakob Magolan*

*Department of Chemistry and Chemical Biology, McMaster University, 1200 Main Street West, Hamilton, Ontario, L8S 3Z5, Canada, Email: magolanjmcmaster.ca

P. Pal, M. Fragis, S. Dharavath, J. W. Johnson, J. Magolan, Synthesis, 2022, 54, 4917-4931.

DOI: 10.1055/a-1868-4148

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Abstract

Wittig olefination of thioalkylphosphonium salts provides vinyl sulfides, that can be 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.

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Key Words

vinyl sulfides, Fischer indole synthesis, azaindoles, thioalkylphosphonium salts

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ID: J66-Y2022