Methods for the synthesis of N-aryl sulfonamides from nitroarenes: an overview

Abstract

Sulfonamides are important pharmacophores found in many human and veterinary medicines. Over 70 FDA-approved drugs contain this privileged structural motif and are used to treat a wide range of conditions, from acne to typhoid fever to pneumonia in HIV/AIDS patients. Interestingly, one-fourth of currently marketed sulfonamide-containing drugs are N-(hetero)aryl sulfonamide derivatives. Therefore, looking for new methodologies for their preparation from inexpensive, easily accessible, and non-toxic starting materials is very important in organic chemistry. Aromatic nitro compounds are valuable intermediates in organic synthesis and widely serve as precursors to amines, hydroxylamines, imines, amides, aldehydes, carboxylic acids, isocyanates and various aza heterocycles. In recent years, various protocols have been established for the synthesis of N-aryl sulfonamides directly from stable and abundant nitroarenes. The purpose of this review is to provide an overview of the available literature on the synthesis of N-(hetero)aryl sulfonamides from the corresponding nitro(hetero)arenes. Literature has been surveyed from 2015 to the end of July 2020.

GRAPHICAL ABSTRACT

KEYWORDS:

• N-(hetero)aryl sulfonamides
• nitro(hetero)arenes
• sodium sulfonates
• sulfonyl chlorides
• arylboronic acids

Disclosure statement

No potential conflict of interest was reported by the author(s).