title: Benzhydrylamines via base-mediated intramolecular sp(3) C-arylation of N-benzyl-2-nitrobenzenesulfonamides--advanced intermediates for the synthesis of nitrogenous heterocycles.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, Institute of Molecular and Translational Medicine, Faculty of Science, Palacký University , 17. Listopadu 12, 771 46 Olomouc, Czech Republic.
authors.forename: Ksenija
authors.initials: K
authors.lastname: Kisseljova
authors.forename: Petra
authors.initials: P
authors.lastname: Smyslová
authors.forename: Viktor
authors.initials: V
authors.lastname: Krchňák
mesh_terms: D000438:Alcohols / Q000737:chemistry; D001559:Benzhydryl Compounds / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007191:Indazoles / Q000138:chemical synthesis; D007202:Indicators and Reagents; D011799:Quinazolines / Q000138:chemical synthesis
chemical_list: D000438:Alcohols; D001559:Benzhydryl Compounds; D001593:Benzyl Compounds; D006571:Heterocyclic Compounds; D007191:Indazoles; D007202:Indicators and Reagents; D011799:Quinazolines; C004531:benzhydrylamine
keywords: C−C bond formation; arylation; benzhydrylamine; heterocycle; indazole oxide; nitrobenzenesulfonamides; quinazoline