Base-Mediated Intramolecular C- and N-Arylation of N,N-Disubstituted 2-Nitrobenzenesulfonamides: Advanced Intermediates for the Synthesis of Diverse Nitrogenous Heterocycles

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.