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Issue 57, 2018
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Calixarene alpha-ketoacetylenes: versatile platforms for reaction with hydrazine nucleophile

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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.

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

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Supplementary files

Article information


Submitted
27 Jul 2018
Accepted
15 Sep 2018
First published
21 Sep 2018

This article is Open Access

RSC Adv., 2018,8, 32765-32769
Article type
Paper

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

A. A. Muravev, S. E. Solovieva, F. B. Galieva, O. B. Bazanova, I. Kh. Rizvanov, K. A. Ivshin, Olga N. Kataeva, S. E. Matthews and I. S. Antipin, RSC Adv., 2018, 8, 32765
DOI: 10.1039/C8RA06349D

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