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

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

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