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Calixarene alpha-ketoacetylenes: versatile platforms for reaction with hydrazine nucleophile

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  • Anton A. Muravev
  • Svetlana E. Solovieva
  • Farida B. Galieva
  • Olga B. Bazanova
  • Ildar Kh. Rizvanov
  • Kamil A. Ivshin
  • Olga N. Kataeva
  • Susan E. Matthews
  • Igor S. Antipin

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Abstract

Late stage diversification of calix[4]arenes and thiacalix[4]arenes with heterocycles remains a significant synthetic challenge and hampers further exploitation of the scaffolds. Here we describe the development of a short and facile synthetic route to conformationally diverse novel calix[4]arene and thiacalix[4]arene ynones using a palladium cross coupling approach (5% Pd(II) + 10% Cu(I)) with benzoyl chloride. Their successful conversion to heterocycles to afford pyrazoles was demonstrated through treatment with hydrazine. Functionalisation is calixarene conformation and linker independent enabling access to a library of structures.

Details

Original languageEnglish
Pages (from-to)32765-32769
JournalRSC Advances
Volume8
Issue number57
DOIs
Publication statusPublished - 21 Sep 2018
Peer-reviewedYes

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