Calixarene alpha-ketoacetylenes: versatile platforms for reaction with hydrazine nucleophile
Anton A Muravev1, Svetlana E Solovieva1,2, Farida B Galieva2
1Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS Kazan 420088 Russia antonm@iopc.ru svsol@iopc.ru.
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.
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