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Copper‐Catalyzed N ‐Arylation of Polysubstituted Pyridines Synthesized by the Novel Reaction of N ‐Sulfonyl Ketenimine and Malononitrile‐Trichloroacetonitrile Adduct
Author(s) -
Nematpour Manijeh,
Fasihi Dastjerdi Hossein,
Mahboubi Rabbani Sayyed Mohammad Ismaeil,
Tabatabai Sayyed Abbas
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3668
Subject(s) - malononitrile , chemistry , ketenimine , aryl , catalysis , sulfonyl , acetonitrile , tetrahydrofuran , medicinal chemistry , iodide , organic chemistry , alkyl , adduct , solvent , halide , polymer chemistry
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 “NH 2 ” 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.