Synthesis, characterisation and metal ion binding properties of crown ethers incorporating 4,5-dioxyxanthones

Cox, Brian G.; Hurwood, Tracey V.; Prodi, Luca; Montalti, Marco; Bolletta, Fabrizio; Watt, C. Ian F.

doi:10.1039/a806487c

Cited by 11 publications

(19 citation statements)

References 31 publications

(43 reference statements)

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“…This method was combined with important adjustments to the Ullmann reaction accomplished by Jackson et al [75] to obtain 1,2-dihydroxyxanthone (16) by a direct lithiation [76] of the unprotected diaryl intermediate 2-(3',4'-dimethoxyphenoxy) benzoic acid (21) (Scheme 5 c)) [67,77]. A direct lithiation has also been applied to synthesize 4,5-dihydroxyxanthone to be incorporated in crown-ether macrocycles (see Section 3.2) [78]. Kristensen et al have described a ring closure of diphenyl ethers via an anionic cascade process initiated by a bromine-lithium exchange, using tert-butyllithium at -78°C , and thus prepared xanthones and related compounds in high yields (Scheme 6) [79]; the reaction proceeded via a sequential intramolecular trapping of a very reactive organolithium intermediate (22).…”

Section: Modifications To the Classical Methodsmentioning

confidence: 97%

“…their incorporation into the crown ethers (112)(113) or related structures would yield ionophores with desirable features [78].…”

Section: Miscellaneous Xanthonesmentioning

confidence: 99%

“…Moreover, syntheses of crown ethers with an incorporated xanthonic core have already been described [78,140,[170][171][172]. An efficient preparation of 4,5-dioxyxanthone (112) [78] and 1,8-dioxyxanthone derivatives (113) [171,172] was accomplished by attachment of an appropriate polyethylene oxide chain to the corresponding dihydroxyxanthones with the incorporation into crown ethers with 18-, 21-, and 24-membered macrocyclic arrays (n = 3, 4, and 5) (Fig.…”

Section: Miscellaneous Xanthonesmentioning

confidence: 99%

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Synthesis of Xanthones: An Overview

Sousa¹,

Pinto

2005

CMC

124

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Among the known synthetic routes to obtain xanthones, the Grover, Shah, and Shah reaction, the cyclodehydration of 2, 2'-dihydroxybenzophenones and electrophilic cycloacylation of 2-aryloxybenzoic acids are the most popular methods. Due to important biological applications of xanthones, some synthetic strategies leading to more complex derivatives have been widely explored in the past years. Thus, the purpose of this review is to report some recent improvements of the classical synthetic methods as well as of some non-classical methods to obtain simple oxygenated xanthones. The strategies for introduction of substituents into the xanthonic nucleus are also summarized. Furthermore, different approaches used to synthesize complex structures, with an emphasis on the total synthesis of bioactive natural products, accomplished in the last twenty years, are also discussed. Besides the synthesis of xanthones, the reactivity of the xanthonic nucleus and its role as a key intermediate for the synthesis of other important classes of compounds are also highlighted.

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Section: Modifications To the Classical Methodsmentioning

confidence: 97%

“…their incorporation into the crown ethers (112)(113) or related structures would yield ionophores with desirable features [78].…”

Section: Miscellaneous Xanthonesmentioning

confidence: 99%

Section: Miscellaneous Xanthonesmentioning

confidence: 99%

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Synthesis of Xanthones: An Overview

Sousa¹,

Pinto

2005

CMC

124

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“…Tricyclic arrays such as xanthene, acridine and anthracene offer an appropriate combination of functionalities, and we have prepared a number of crowns incorporating such arrays (Cox et al, 1995;Cox et al, 1999). The present paper describes the structure determination of the alcohol (1) ( Fig.…”

Section: Introductionmentioning

confidence: 98%

X-ray and neutron structure of 1,8-(3,6,9-trioxaundecane-1,11-diyldioxy)-9,10-dihydro-10,10-dimethylanthracene-9-ol (P326); some pitfalls of automatic data collection

Palmer

Potter

Lisgarten

et al. 2001

Acta Crystallogr Sect B

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The structure of the crown ether 1,8-(3,6,9-trioxaundecane-1,11-diyldioxy)-9,10-dihydro-10,10-dimethylanthracene-9-ol, C(24)H(30)O(6).H(2)O (1), code name P326, the parent compound for a series of derivatives, has been determined by both X-ray diffraction at room temperature and neutron diffraction at very low temperature. The unit cells are very similar at both temperatures and in both cases the crystals exhibit P2(1) symmetry with Z = 4 (two molecules, A and B, respectively, per asymmetric unit) and pseudosymmetry P2(1)/c. The higher symmetry is broken mainly by the two independent water molecules in the unit cell, some reflections which would be absent in P2(1)/c having strong intensities in both the X-ray and neutron data. In both molecules A and B hydrogen bonds involving the water molecule stabilize the macrocyclic ring structure, one involving the macrocyclic O(9) as a donor. Close contacts between the water and macrocyclic O atoms in each molecule also suggest the presence of two bifurcated hydrogen bonds, involving water HW2 to both O(16) and O(18), and water HW1 to both O(18) and O(20), respectively, with considerable variation in the geometry being present. Both molecules A and B exhibit very close pseudosymmetry across a plane perpendicular to the molecular plane and through atoms C(9) and O(18), and in addition are predominantly planar structures. The X-ray analysis failed to reveal one H atom per water molecule, each being subsequently included after location and refinement in the neutron analysis.

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“…Moreover the properties of the donor atoms in the heterocycle can easily be modified by substitution in the aromatic rings, and these derivatives can also be chromo-or fluorogenic, making them effective optical sensor molecules. Synthesis and molecular recognition studies of many crown ethers based on tricyclic heterocycles are reported in the literature, for example those of xanthone 10 -, dibenzofuran [11][12][13][14] -, phenanthroline [15][16][17][18][19][20][21][22] -, phenazine [23][24][25][26][27] -, or acridone-and acridine 23,[28][29][30][31][32][33][34][35][36][37] -based macrocycles. In the continuation of our research of crown ethers based on tricyclic ring systems, [23][24][25][26][27][28][29][30][31][32][33][34][35][36][37] our attention turned toward phenothiazine.…”

Section: Introductionmentioning

confidence: 99%