Solid-phase synthesis of 2-aryl-3-alkylamino-1H-indoles from 2-nitro-N-(2-oxo-2-arylethyl)benzenesulfonamides via base-mediated C-arylation
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
25547263
DOI
10.1021/co500167g
Knihovny.cz E-resources
- Keywords
- C-arylation, advanced intermediates, heterocycles, indoles, solid-phase synthesis,
- MeSH
- Cyclization MeSH
- Indoles chemical synthesis chemistry MeSH
- Molecular Structure MeSH
- Sulfonamides chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Indoles MeSH
- Sulfonamides MeSH
Polymer-supported 2-nitro-N-(2-oxo-2-arylethyl)benzenesulfonamides, prepared from resin-bound amines by sulfonylation with 2-nitrobenzenesulfonyl chlorides followed by alkylation with α-bromoacetophenones, represent advanced intermediates for the synthesis of different nitrogenous heterocycles. We report their application for the synthesis of 2-aryl-3-alkylamino-1H-indoles via base-mediated C-arylation reactions followed by the reduction of the C-arylated intermediates. Linear precursors for C-arylation were prepared on solid-phase support from simple, commercially available building blocks. The effects of different substituents on the amino and aryl groups were addressed.
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