Copper‐Catalyzed N‐Arylation of Polysubstituted Pyridines Synthesized by the Novel Reaction of N‐Sulfonyl Ketenimine and Malononitrile‐Trichloroacetonitrile Adduct

Abstract

In this study, we synthesized some new derivatives of N‐(4‐amino‐5‐cyano‐6‐(trichloromethyl)pyridin‐2‐yl)alkyl sulfonamides in the presence of a copper catalyst. A one‐pot reaction system was used, and four components participated in the process. These four components were sulfonyl azides, terminal alkynes, malononitrile, and trichloroacetonitrile. The reaction rate was increased by the use of copper (I) iodide as the catalyst and tetrahydrofuran was used as the solvent. We achieved the final compounds in moderate to good yields. Moreover, we converted “NH2” side group to N‐aryl by the use of various aryl halide analogs in acetonitrile as the solvent, under mild reaction and at the room temperature.

N‐Heteroarylation of Sulfonamides: An Overview

“…In the year 2019, Tabatabai et al [38] . gave a method to synthesize derivatives of N ‐(4‐amino‐5‐cyano‐6‐(trichloromethyl)pyridin‐2‐yl)alkyl sulfonamides using copper catalyst.…”

“…In the year 2019, Tabatabai et al [38] gave a method to synthesize derivatives of N-(4-amino-5-cyano-6-(trichloromethyl)pyridin-2-yl)alkyl sulfonamides using copper catalyst. They employed a one-pot synthesis method with four components, which were terminal…”