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ACS Comb Sci. 2014 Sep 8;16(9):500-5. doi: 10.1021/co5000739. Epub 2014 Aug 8.

Base-mediated intramolecular C- and N-arylation of N,N-disubstituted 2-nitrobenzenesulfonamides: advanced intermediates for the synthesis of diverse nitrogenous heterocycles.

Author information

1
Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University , 17. Listopadu 12, 771 46 Olomouc, Czech Republic.

Abstract

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.

KEYWORDS:

C−C bond formation; arylation; diversity-oriented synthesis; heterocycle; nitrobenzenesulfonamides

PMID:
25076047
DOI:
10.1021/co5000739
[Indexed for MEDLINE]

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