One-Step Synthesis of Sulfonamides from N-Tosylhydrazones

Abstract

The first described reaction between N-tosylhydrazone and SO2 is reported to provide alkyl sulfonamides in the presence of various amines. In this procedurally simple method, hydrazones of both unsaturated aldehydes and ketones proceed in moderate to excellent yields. Primary and secondary aliphatic amines are accommodated in this reaction, which provides a novel route to sulfonamides.

Versatile Synthesis of 4‐Aryl Chroman and 1‐Aryl Tetralins Through Metal‐Free Reductive Arylations

“…K 3 PO 4 promoted this thermolytic cross‐coupling about 39 %, but Cs 2 CO 3 seemed optimal (Table , entry‐4, 5). Organic bases remained ineffective and N‐alkylated products became dominant when any nucleophilic base was used (Table , entry‐ 6, 7) . Molecular sieves and additives such as ( n Bu) 4 NI, KI were already proved detrimental for this coupling.…”

Efficient and Sustainable Synthesis of a Potent and Selective 5-HT7 Receptor Antagonist Using a Mechanochemical Approach

“…Various accessible methods to form sulfonamide bond in conventional solution or on solid support have been extensively reported in literature. [35][36][37][38][39][40] However, most of them involve the use of strong organic base, excess of sulfonylating agent, and low environmental friendly solvents (in particular dichloromethane). To develop a more sustainable and efficient methodology, sulfonylation of intermediate 4 with 3chlorobenzenesulfonyl chloride was optimized under milling conditions.…”

An Update of N-Tosylhydrazones: Versatile Reagents for Metal-Catalyzed and Metal-Free Coupling Reactions

“…121 In 2016, Tsai and co-workers reported a three-component reaction between N-tosylhydrazone, amines, and sulfur dioxide to provide alkanesulfonamides. 122 With the solid adduct DABSO [1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide)] as the precursor of sulfur dioxide, this reaction shows excellent compatibility for diverse substituted groups on N-tosylhydrazones.…”