I. R. Mironova (Knyazeva), N. P. Romashov, V. V. Syakaev, D. P. Gerasimova, O. A. Lodochnikova, A. R. Burilov, “Synthesis and structural features of new calix[4]resorcinols with anthracene- and pyrene-ended isoxazole-containing fragments”, Mendeleev Commun., 2024, Volume 34, Issue 3,Pages <nobr>392

Communications

Synthesis and structural features of new calix[4]resorcinols with anthracene- and pyrene-ended isoxazole-containing fragments

I. R. Mironova (Knyazeva)^a, N. P. Romashov^b, V. V. Syakaev^a, D. P. Gerasimova^a, O. A. Lodochnikova^a, A. R. Burilov^a

^a A.E. Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of the Russian Academy of Sciences, Kazan, Russian Federation
^b Kazan National Research Technological University, Kazan, Russian Federation

Abstract: Reactions between 4-(propargyloxy)benzaldehyde with anthracene-9-carbaldehyde oxime or pyrene-1-carbaldehyde oxime in the presence of chloramine T in ethanol lead to new isoxazole-containing derivatives of benzaldehyde. The subsequent acid-catalyzed condensation of these compounds with 2-methylresorcinol in chloroform/trifluoroacetic acid mixtures affords novel calix[4]resorcinols with anthaceneand pyrene-ended isoxazole-containing fragments as all–cis (rccc) and cis–trans–trans (rctt) diastereoisomers, their ratios being dependent on the CF₃CO₂H percentage in the medium. The crystal structures of pyrene-ended isoxazole-containing benzaldehyde and corresponding calix[4]resorcinol rctt isomer have been established by single crystal X-ray diffraction.

Keywords: calix[4]resorcinols, condensation, isoxazole, anthracene, pyrene, diastereoisomer.

Language: English

DOI: 10.1016/j.mencom.2024.04.025

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