title: Base-mediated intramolecular C- and N-arylation of N,N-disubstituted 2-nitrobenzenesulfonamides: advanced intermediates for the synthesis of diverse nitrogenous heterocycles.
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.
authors: Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University , 17. Listopadu 12, 771 46 Olomouc, Czech Republic.
authors: Petra
authors: P
authors: Smyslová
authors: Ksenija
authors: K
authors: Kisseljova
authors: Viktor
authors: V
authors: Krchňák
mesh_terms: D002244:Carbon / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D009584:Nitrogen / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D006571:Heterocyclic Compounds; D009574:Nitro Compounds; D013449:Sulfonamides; D002244:Carbon; D009584:Nitrogen
keywords: C−C bond formation; arylation; diversity-oriented synthesis; heterocycle; nitrobenzenesulfonamides