Base-mediated intramolecular C- and N-arylation of N,N-disubstituted 2-nitrobenzenesulfonamides: advanced intermediates for the synthesis of diverse nitrogenous heterocycles
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
25076047
DOI
10.1021/co5000739
Knihovny.cz E-resources
- Keywords
- C−C bond formation, arylation, diversity-oriented synthesis, heterocycle, nitrobenzenesulfonamides,
- MeSH
- Nitrogen chemistry MeSH
- Nitro Compounds chemistry MeSH
- Heterocyclic Compounds chemical synthesis chemistry MeSH
- Molecular Structure MeSH
- Sulfonamides chemistry MeSH
- Carbon chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Nitrogen MeSH
- Nitro Compounds MeSH
- Heterocyclic Compounds MeSH
- Sulfonamides MeSH
- Carbon MeSH
Structural and electronic features that facilitate and direct the intramolecular C- and N-arylation of 2-alkyl-2-{[N-(benzyl)-2-nitrophenyl]sulfonamido}acetic acid esters and amides were examined. The substitution pattern and amino acid carboxy-terminal functionality determined the arylation position. C/N-arylated products represent advanced intermediates for combinatorial synthesis of diverse nitrogenous heterocycles, including indazoles, quinazolinones, quinoxalinones, and 3-amino-2-oxindoles.
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