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Synthesis 2022; 54(22): 4917-4931
DOI: 10.1055/a-1868-4148
DOI: 10.1055/a-1868-4148
feature
Use of Vinyl Sulfides in Fischer Indole Reactions
This research was supported by a Natural Sciences and Engineering Research Council of Canada (NSERC) Discovery Grant (RGPIN-2018-06438), the McMaster University’s Faculty of Health Sciences Dean’s Fund, and by a generous endowed gift from the Boris Family. M.F. was supported by a Canada Graduate Scholarship (CGS-M).
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 saltsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1868-4148.
- Supporting Information
Publication History
Received: 13 April 2022
Accepted after revision: 02 June 2022
Accepted Manuscript online:
02 June 2022
Article published online:
12 July 2022
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