Ionic liquid-supported synthesis of sulfonamides and carboxamides

Manoj Kumar Muthayala, Bhupender S. Chhikara, Keykavous Parang, Anil Kumar

Research output: Contribution to journalArticlepeer-review

Abstract

An ionic liquid-supported aldehyde was designed and converted to ionic liquid-supported secondary aryl amines through reductive amination. The reaction of ionic liquid-supported aryl amines with sulfonyl chlorides and acid chlorides, respectively, followed by cleavage using trifluoroacetic acid (TFA) afforded sulfonamides and caboxamides. To introduce additional diversity in the synthesis of sulfonamides and caboxamides, ionic liquid-supported iodosubstituted aryl amine was synthesized using the same strategy, and underwent Suzuki coupling reaction, followed by reaction with a methanesulfonyl chloride to generate the corresponding biaryl sulfonamide. The advantages of the protocol over solid-phase synthesis are homogeneous reaction medium, high loading, easy separation of products, and characterization of intermediates.

Original languageEnglish (US)
Pages (from-to)60-65
Number of pages6
JournalACS Combinatorial Science
Volume14
Issue number1
DOIs
StatePublished - Jan 9 2012
Externally publishedYes

Keywords

  • Carboxamides
  • ionic liquids
  • parallel synthesis
  • sulfonamides
  • Suzuki coupling reaction

ASJC Scopus subject areas

  • Chemistry(all)

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