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Direct α-Imination of N-Acyl Pyrazoles with Nitrosoarenes

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  • Chiara Volpe, Univ Salerno, University of Salerno, Dipartimento Chim & Biol
  • ,
  • Sara Meninno, Univ Salerno, University of Salerno, Dipartimento Chim & Biol
  • ,
  • Giulia Mirra, Univ Salerno, University of Salerno, Dipartimento Chim & Biol
  • ,
  • Jacob Overgaard
  • Amedeo Capobianco, Univ Salerno, University of Salerno, Dipartimento Chim & Biol
  • ,
  • Alessandra Lattanzi, Univ Salerno, University of Salerno, Dipartimento Chim & Biol

Unprecedented alpha-imino N-acyl pyrazoles were efficiently and selectively prepared through the 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD)-catalyzed reaction of nitrosoarenes with N-acyl pyrazoles via an N-nitroso aldol reaction/dehydration sequence. The alpha-imino acyl pyrazoles were demonstrated to be new versatile intermediates for practical one-pot syntheses of alpha-imino amides, dipeptide precursors, esters, and beta-amino alcohols. The synthetic method competes with known protocols in terms of ready availability of the reagents and catalyst, mild and catalytic reaction conditions, gram-scale applicability, and scope of the alpha-imino acid derivatives achievable.

Original languageEnglish
JournalOrganic Letters
Volume21
Issue13
Pages (from-to)5305-5309
Number of pages5
ISSN1523-7060
DOIs
Publication statusPublished - Jul 2019

    Research areas

  • ACID-CATALYZED REDUCTION, IMINO-ESTERS, ENANTIOSELECTIVE SYNTHESIS, EFFICIENT SYNTHESIS, DIASTEREOSELECTIVE SYNTHESIS, TRANSFER HYDROGENATION, NUCLEOPHILIC-ADDITION, ASYMMETRIC-SYNTHESIS, AMINO, NITROSOBENZENE

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