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:
magolanj
mcmaster.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
ID: J66-Y2022
