Synthesis and spectral study of N,N-diethyl-2-methyl-1-tosylpyrrolidine-2-carboxamide and functionalized sulfonamide scaffolds.

Abstract

Background and Objective: Sulfonamides are known to represent a class of medicinally important compounds and chemical intermediates, which are extensively used in drug development. The aim of this present study is to synthesize a series of arylsulfonamide-based dialkylated amide motifs. Materials and Methods: In this study, the design and development of arylsulfonamide pharmacophore bearing N,N-diethyl substituted amide moieties 2a-k was achieved in improved yields using non-conventional amidation of p-tolylsulfonamide precursors 1a-k. The structures of the compounds were substantiated based on the results of elemental analysis and spectroscopic data namely, FT-IR, 1H-NMR, 13C-NMR and mass spectra. Results: The series of targeted compounds were synthesized in good to excellent yields and subsequently purified by column chromatography where necessary. Conclusion: The synthesis of arylsulfonamide-based dialkylated amide motifs was successfully achieved. These compounds may serve as versatile intermediates that pave ways toward achieving diverse bioactive heterocyclic compounds for future drug discovery and development.