I. R. Knyazeva, V. V. Syakaev, W. D. Habicher, A. R. Burilov, “New calix[4]resorcinol <i>rccc</i> diastereoisomer with terminal triple bonds: Synthesis, structural features and reactions”, Mendeleev Commun., 2023, Volume 33, Issue 3,Pages <nobr>397

This article is cited in 2 papers

Communications

New calix[4]resorcinol rccc diastereoisomer with terminal triple bonds: Synthesis, structural features and reactions

I. R. Knyazeva^a, V. V. Syakaev^a, W. D. Habicher^b, 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 Institute of Organic Chemistry, Dresden University of Technology, Dresden, Germany

Abstract: One-pot acid-catalyzed cyclocondensation of 2-methyl-resorcinol with 4-(propargyloxy)benzaldehyde in CHCl₃/CF₃CO₂H media affords all-cis (rccc) and/or cis-trans-trans (rctt) calix[4]resorcinol diastereomers bearing four terminal alkyne groups at aromatic substituents, the isomer ratio and yield being dependent on the CHCl₃/CF₃CO₂H ratio. The rctt isomer (kinetic control product) can be converted to thermodynamically more stable rccc isomer at prolonged refluxing in CHCl₃/CF₃CO₂H mixture. The rccc diastereomer was subjected to additional propargylation followed by the click reactions with benzylic azides to afford new highly triazolated calix[4]resorcinols.

Keywords: calixresorcinols, condensation, diastereoisomers, conformation, click reaction, 1,2,3-triazoles.

Language: English

DOI: 10.1016/j.mencom.2023.04.031

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