Benzhydrylamines via base-mediated intramolecular sp(3) C-arylation of N-benzyl-2-nitrobenzenesulfonamides--advanced intermediates for the synthesis of nitrogenous heterocycles
Language English Country United States Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
25180543
DOI
10.1021/co500098y
Knihovny.cz E-resources
- Keywords
- C−C bond formation, arylation, benzhydrylamine, heterocycle, indazole oxide, nitrobenzenesulfonamides, quinazoline,
- MeSH
- Alcohols chemistry MeSH
- Benzhydryl Compounds chemistry MeSH
- Benzyl Compounds chemistry MeSH
- Quinazolines chemical synthesis MeSH
- Heterocyclic Compounds chemical synthesis MeSH
- Indazoles chemical synthesis MeSH
- Indicators and Reagents MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Alcohols MeSH
- benzhydrylamine MeSH Browser
- Benzhydryl Compounds MeSH
- Benzyl Compounds MeSH
- Quinazolines MeSH
- Heterocyclic Compounds MeSH
- Indazoles MeSH
- Indicators and Reagents MeSH
N-Benzyl-2-nitrobenzenesulfonamides underwent base-mediated intramolecular arylation at the benzyl sp(3) carbon to yield benzhydrylamines. The presence of electron withdrawing groups on the aromatic ring of the benzyl group was required to facilitate the C-arylation. Unsymmetrically substituted benzhydrylamines are advanced intermediates toward nitrogenous heterocycles, as exemplified in the syntheses of indazole oxides and quinazolines.
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