Formation of a hydrogen-bonded barbiturate [2]-rotaxane

Arnaud Tron; Peter J Thornton; Mathias Rocher; Henri-Pierre Jacquot de Rouville; Jean-Pierre Desvergne; Brice Kauffmann; Thierry Buffeteau; Dominique Cavagnat; James H R Tucker; Nathan D McClenaghan

doi:10.1021/ol500099u

Formation of a hydrogen-bonded barbiturate [2]-rotaxane

Arnaud Tron, Peter J Thornton, Mathias Rocher, Henri-Pierre Jacquot de Rouville, Jean-Pierre Desvergne, Brice Kauffmann, Thierry Buffeteau, Dominique Cavagnat, James H R Tucker, Nathan D McClenaghan

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

21 Citations (Scopus)

Abstract

Interlocked structures containing the classic Hamilton barbiturate binding motif comprising two 2,6-diamidopyridine units are reported for the first time. Stable [2]-rotaxanes can be accessed either through hydrogen-bonded preorganization by a barbiturate thread followed by a Cu(+)-catalyzed "click" stoppering reaction or by a Cu(2+)-mediated Glaser homocoupling reaction.

Original language	English
Pages (from-to)	1358-61
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	5
DOIs	https://doi.org/10.1021/ol500099u
Publication status	Published - 7 Mar 2014

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abstract = "Interlocked structures containing the classic Hamilton barbiturate binding motif comprising two 2,6-diamidopyridine units are reported for the first time. Stable [2]-rotaxanes can be accessed either through hydrogen-bonded preorganization by a barbiturate thread followed by a Cu(+)-catalyzed {"}click{"} stoppering reaction or by a Cu(2+)-mediated Glaser homocoupling reaction.",

author = "Arnaud Tron and Thornton, {Peter J} and Mathias Rocher and {Jacquot de Rouville}, Henri-Pierre and Jean-Pierre Desvergne and Brice Kauffmann and Thierry Buffeteau and Dominique Cavagnat and Tucker, {James H R} and McClenaghan, {Nathan D}",

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T1 - Formation of a hydrogen-bonded barbiturate [2]-rotaxane

AU - Tron, Arnaud

AU - Thornton, Peter J

AU - Rocher, Mathias

AU - Jacquot de Rouville, Henri-Pierre

AU - Desvergne, Jean-Pierre

AU - Kauffmann, Brice

AU - Buffeteau, Thierry

AU - Cavagnat, Dominique

AU - Tucker, James H R

AU - McClenaghan, Nathan D

PY - 2014/3/7

Y1 - 2014/3/7

N2 - Interlocked structures containing the classic Hamilton barbiturate binding motif comprising two 2,6-diamidopyridine units are reported for the first time. Stable [2]-rotaxanes can be accessed either through hydrogen-bonded preorganization by a barbiturate thread followed by a Cu(+)-catalyzed "click" stoppering reaction or by a Cu(2+)-mediated Glaser homocoupling reaction.

AB - Interlocked structures containing the classic Hamilton barbiturate binding motif comprising two 2,6-diamidopyridine units are reported for the first time. Stable [2]-rotaxanes can be accessed either through hydrogen-bonded preorganization by a barbiturate thread followed by a Cu(+)-catalyzed "click" stoppering reaction or by a Cu(2+)-mediated Glaser homocoupling reaction.

U2 - 10.1021/ol500099u

DO - 10.1021/ol500099u

M3 - Article

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SN - 1523-7060

VL - 16

SP - 1358

EP - 1361

JO - Organic Letters

JF - Organic Letters

IS - 5

ER -

Formation of a hydrogen-bonded barbiturate [2]-rotaxane

Abstract

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