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

doi:10.1016/j.tet.2011.07.022

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

Chemistry

Research output: Contribution to journal › Article › peer-review

16 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 language	English
Pages (from-to)	7027-7034
Number of pages	8
Journal	Tetrahedron
Volume	67
Issue number	37
DOIs	https://doi.org/10.1016/j.tet.2011.07.022
State	Published - 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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10.1016/j.tet.2011.07.022

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

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.",

keywords = "Atropisomerism, Azides, Calixarenes, Click chemistry",

author = "Hardman, {Michael J.} and Thomas, {Ashley M.} and Carroll, {Louise T.} and Williams, {Linus C.} and Sean Parkin and Fantini, {Jordan L.}",

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. ",

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doi = "10.1016/j.tet.2011.07.022",

language = "English",

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AU - Hardman, Michael J.

AU - Thomas, Ashley M.

AU - Carroll, Louise T.

AU - Williams, Linus C.

AU - Parkin, Sean

AU - Fantini, Jordan L.

N1 - 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.

PY - 2011/9/16

Y1 - 2011/9/16

N2 - 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.

AB - 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.

KW - Atropisomerism

KW - Azides

KW - Calixarenes

KW - Click chemistry

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ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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