Benzhydrylamines via Base-Mediated Intramolecular sp3 C-Arylation of N-Benzyl-2-nitrobenzenesulfonamides鈥擜dvanced Intermediates for the Synthesis of Nitrogenous Heterocycles
N-Benzyl-2-nitrobenzenesulfonamides underwent base-mediated intramolecular arylation at the benzyl sp3 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.
Keywords:
arylation; benzhydrylamine; C鈭扖 bond formation; heterocycle; indazole oxide; nitrobenzenesulfonamides; quinazoline