Use of Vinyl Sulfides in Fischer Indole Reactions Journal Articles

abstract

• AbstractVinyl 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.

authors

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

status

• published 

publication date

• November 2022

has subject area

• 0301 Analytical Chemistry (FoR)
• 0305 Organic Chemistry (FoR)
• Organic Chemistry (Science Metrix)

published in

• Synthesis  Journal

keywords

• ACCESS
• Chemistry
• Chemistry, Organic
• DISCOVERY
• ENOL ETHERS
• ETHYL PYRUVATE
• Fischer indole synthesis
• INDOLIZATION
• MECHANISM
• Physical Sciences
• Science & Technology
• Wittig olefination
• azaindole
• thioalkylphosphonium salts
• vinyl sulfide

Digital Object Identifier (DOI)

• 10.1055/a-1868-4148

start page

• 4917

end page

• 4931

volume

• 54

issue

• 22