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

Muravev, Anton A., Solovieva, Svetlana E., Galieva, Farida B., Bazanova, Olga B., Rizvanov, Ildar Kh., Ivshin, Kamil A., Kataeva, Olga N., Matthews, Susan E. ORCID: and Antipin, Igor S. (2018) Calixarene alpha-ketoacetylenes: versatile platforms for reaction with hydrazine nucleophile. RSC Advances, 8 (57). pp. 32765-32769. ISSN 2046-2069

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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.

Item Type: Article
Faculty \ School: Faculty of Science > School of Pharmacy
Faculty of Science > School of Natural Sciences
UEA Research Groups: Faculty of Science > Research Groups > Chemical Biology and Medicinal Chemistry (former - to 2021)
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Depositing User: LivePure Connector
Date Deposited: 12 Oct 2018 09:30
Last Modified: 05 May 2024 01:39
DOI: 10.1039/C8RA06349D


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