Synthesis and click cycloaddition reactions of tetramethoxy- and tetrapropoxy-2-(ω-azidoalkyl)calix[4]arenes

Michael J. Hardman, Ashley M. Thomas, Louise T. Carroll, Linus C. Williams, Sean Parkin, Jordan L. Fantini

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

2-(ω-Chloroalkyl)tetramethoxycalix[4]arenes are converted to 2-(ω-azidoalkyl)tetramethoxy- and cone-2-(ω-azidoalkyl) tetrapropoxycalix[4]arenes, the former by substitution and the latter by demethylation to 2-(ω-chloroalkyl)tetrahydroxycalix[4]arenes, which are O-propylated before substitution of azide for chloride. The azide-terminated calixarenes undergo Cu(I)-catalyzed 1,3-cycloaddition to terminal alkynes to give 1,4-disubstituted 1,2,3-triazoles, demonstrating the potential to couple calixarenes from a tether at the 2-position (methylene bridge) to substrates that bear a terminal alkyne group. The cone conformation of cone-2-(4- chlorobutyl)tetrapropoxycalix[4]arene has been confirmed by X-ray diffraction.

Original languageEnglish
Pages (from-to)7027-7034
Number of pages8
JournalTetrahedron
Volume67
Issue number37
DOIs
StatePublished - Sep 16 2011

Bibliographical note

Funding Information:
We thank Drs. Thomas A. Evans and Joseph J. Reczek for helpful comments. Support for this research by the Denison University and the Denison University Research Foundation is gratefully acknowledged.

Keywords

  • Atropisomerism
  • Azides
  • Calixarenes
  • Click chemistry

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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