Synthesis of β-cydodextrin derivatives functionalized with azobenzene

被引：29

作者：

Casas-Solvas, Juan M. ^{[1
]}

Martos-Maldonado, Manuel C. ^{[1
]}

Vargas-Berenguel, Antonio ^{[1
]}

机构：

[1] Univ Almeria, Area Quim Organ, Almeria 04120, Spain

来源：

TETRAHEDRON | 2008年 / 64卷 / 48期

关键词：

D O I：

10.1016/j.tet.2008.08.098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two approaches for the synthesis of beta-cyclodextrin and bis(beta-cyclodextrin) bearing azobenzene on the primary face are reported. First, the nucleophilic substitution of mono-6-tosyl-beta-cyclodextrin by azobenzene anion derivatives was reinvestigated and found to produce mono-3,6-anhydro-beta-cyclodextrin as a side product. A slight modification of the reported reaction conditions including the use of Cs2CO3 led to a substantial improvement of the yields. In addition, a convenient method based on the application of click chemistry led to 1,2,3-triazole-linked azobenzene-cyclodextrin derivatives in good yields. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：10919 / 10923

页数：5

共 74 条

[1] pH dependent in-out isomerism of an amino-β-cyclodextrin derivative [J].

Alcalde, Mercedes Alvarez ;

Gancedo, Cristina ;

Jover, Aida ;

Carrazana, Jorge ;

Soto, Victor H. ;

Meijide, Francisco ;

Tato, Jose Vazquez .

JOURNAL OF PHYSICAL CHEMISTRY B, 2006, 110 (27) :13399-13404

[2]

[Anonymous], 1999, Supramolecular electrochemistry

[3] Alizarin yellow-modified beta-cyclodextrin as a guest-responsive absorption change sensor [J].

Aoyagi, T ;

Nakamura, A ;

Ikeda, H ;

Ikeda, T ;

Mihara, H ;

Ueno, A .

ANALYTICAL CHEMISTRY, 1997, 69 (04) :659-663

[4] Synthesis and photoisomerization of an azobenzene derivative bearing two β-cyclodextrin units at both ends [J].

Aoyagi, T ;

Ueno, A ;

Fukushima, M ;

Osa, T .

MACROMOLECULAR RAPID COMMUNICATIONS, 1998, 19 (02) :103-105

[5]

BALZANI V, 2003, MOL DEVICES MACHINES, P177

[6] Tuneable fluorescent marker appended to β-cyclodextrin:: a pH-driven molecular switch [J].

Becuwe, Matthieu ;

Cazier, Francine ;

Bria, Marc ;

Woisel, Patrice ;

Delattre, Francois .

TETRAHEDRON LETTERS, 2007, 48 (35) :6186-6188

[7] ELECTRONIC STRUCTURE AND SPECTRA OF CIS- AND TRANS-AZOBENZENE [J].

BEVERIDGE, DL ;

JAFFE, HH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1966, 88 (09) :1948-+

[8]

BILEWICZ R, 2006, CYCLODEXTRINS THEIR, P298

[9] CuI-catalyzed alkyne-azide "click" cycloadditions from a mechanistic and synthetic perspective [J].

Bock, VD ;

Hiemstra, H ;

van Maarseveen, JH .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (01) :51-68

[10] CONFORMATIONAL FEATURES AND COORDINATION PROPERTIES OF FUNCTIONALIZED CYCLODEXTRINS - FORMATION, STABILITY, AND STRUCTURE OF PROTON AND COPPER(II) COMPLEXES OF HISTAMINE-BEARING BETA-CYCLODEXTRIN IN AQUEOUS-SOLUTION [J].

BONOMO, RP ;

CUCINOTTA, V ;

DALESSANDRO, F ;

IMPELLIZZERI, G ;

MACCARRONE, G ;

VECCHIO, G ;

RIZZARELLI, E .

INORGANIC CHEMISTRY, 1991, 30 (13) :2708-2713

← 1 2 3 4 5 6 7 8 →