A novel Sc(OTf) 3 -catalyzed Tiffeneau-Demjanov ring expansion of six-membered cyclic ketones has been developed. The resulting seven-membered cyclic β-keto carboxamides were found to be versatile precursors to rare bicyclic pyrazoles obtained in modest to good yields via condensation with aryl hydrazines in the presence of Lawesson's reagent.

Original languageEnglish
Article numberst-2019-b0609-l
Pages (from-to)373-377
Number of pages5
JournalSynlett
Volume31
Issue number4
DOIs
StatePublished - 3 Mar 2020

    Research areas

  • bicyclic pyrazoles, Lawesson's reagent, scandium triflate, Tiffeneau-Demjanov ring expansion, α-diazoacetamides, β-keto carboxamides, ENTRY, beta-keto carboxamides, CYCLOALKANONES, BIS-OXINDOLES, KETONES, alpha-diazoacetamides, COPPER-MEDIATED CONSTRUCTION, EFFICIENT, HOMOLOGATION, ACCESS, C-H

    Scopus subject areas

  • Organic Chemistry

ID: 52203575