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Synthesis 2015; 47(05): 630-640
DOI: 10.1055/s-0034-1379604
DOI: 10.1055/s-0034-1379604
paper
Synthesis of a Functionalized Polymer Based on a Calix[4]resorcinarene via Covalently Anchored Cationic Moieties: A Reactive Solid Support for Ring Transformation and Expansion of Thiopyrylium Salts
Weitere Informationen
Publikationsverlauf
Received: 08. Oktober 2014
Accepted after revision: 04. November 2014
Publikationsdatum:
18. Dezember 2014 (online)
Abstract
In this work, for the first time, a cationic polymer containing pendant pyridinium groups was synthesized via post-functionalization of the polymeric backbone based on a calix[4]resorcinarene, and characterized by AFM, TEM, analytical CHN, TGA, and DTG techniques. The functionalized polymer is conveniently loaded with desired anions, thereby providing novel and recyclable polymer-supported reagents for achieving synthetic goals. The thermal stability of this cationic polymer (up to 250 °C by TGA) allows thermally demanding ring transformation and expansion of 2,4,6-triarylthiopyrylium salts on its side chains and polymeric backbone without decomposition and leaching of active species in the reaction media. This green method furnished a straightforward route for the synthesis of valuable 2,4,6-triarylpyridines, along with novel 2,5,7-triaryl-1,3-thiazepine derivatives, which are widely present as motifs in an assortment of biologically active molecules.
Key words
azide - green chemistry - heterocycles - nucleophilic addition - polymers - ring expansionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379604.
- Supporting Information
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References
- 1a Donati D, Morelli C, Porcheddu A, Taddei M. J. Org. Chem. 2004; 69: 9316
- 1b Wentworth AD, Wentworth PJr, Mansoor UF, Janda KD. Org. Lett. 2000; 2: 477
- 1c Crosignani S, Gonzalez J, Swinnen D. Org. Lett. 2004; 6: 4579
- 1d Du Y, Cai F, Kong D.-L, He L.-N. Green Chem. 2005; 7: 518
- 1e Park S.-W, Choi B.-S, Park D.-W, Oh K.-J, Lee J.-W. Green Chem. 2007; 9: 605
- 1f Watile RA, Bagal DB, Deshmukh KM, Dhake KP, Bhanage BM. J. Mol. Catal. A: Chem. 2011; 351: 196
- 2 Rao AH. N, Thankamony RL, Kim H.-J, Nam S, Kim T.-H. Polymer 2013; 54: 111
- 3 Gao H, Wang Y, Zheng L. Chem. Eng. J. 2013; 234: 372
- 4a Gaiolas C, Costa AP, Silva M. Cellul. Chem. Technol. 2006; 40: 783
- 4b Gaiolas C, Mendes P, Silva M. Appita J. 2005; 58: 282
- 4c Baba Y. Japan Tappi J. 2001; 55: 11
- 4d Xiao H, Pelton P, Hamielec A. Tappi J. 1996; 79: 129
- 5a Ley SV, Baxendale IR, Bream RN, Jackson PS, Leach AG, Longbottom DA, Nesi M, Scott JS, Storer RI, Taylor SJ. J. Chem. Soc., Perkin Trans. 1 2000; 3815
- 5b Kirschning A, Monenschein H, Wittemberg R. Angew. Chem. Int. Ed. 2001; 40: 650
- 5c Flynn DL, Berk SC, Makara GM. Curr. Opin. Drug Discovery Dev. 2002; 5: 580
- 5d Ley SV, Baxendale IR. Nat. Rev. Drug Discovery 2002; 1: 573
- 5e Yang G, Chen Z, Zhang H. Green Chem. 2003; 5: 441
- 5f Chen J.-M, Zeng X.-M, Middleton K, Zhdankin VV. Tetrahedron Lett. 2011; 52: 1952
- 5g Suzuki Y, Togo H. Synthesis 2010; 2355
- 5h Roche D, Lardy C, Tournier L, Prunier M, Valeur E. Tetrahedron Lett. 2010; 51: 2277
- 5i Brenelli EC. S, Brenelli JA, Pinto RC. L. Synfacts 2005; 172
- 5j Verdié P, Ronga L, Cristau M, Amblard M, Cantel S, Enjalbal C, Puget K, Martinez J, Subra G. Synfacts 2011; 1382
- 5k Togo H, Hirai T. Synthesis 2005; 2664
- 5l Sheng S.-R, Liu X.-L, Wang X.-C, Xin Q. Synthesis 2004; 2833
- 5m Tang E, Chen B, Zhang L, Li W. Synlett 2011; 707
- 6 Mouradzadegun A, Kiasat AR, Kazemian Fard P. Catal. Commun. 2012; 29: 1
- 7a Katritzky AR, Marson CM. Angew. Chem., Int. Ed. Engl. 1984; 23: 420
- 7b Eryazici I, Moorefield CN, Durmus S, Newkome GR. J. Org. Chem. 2006; 71: 1009
- 7c Zhou Y, Kijima T, Kuwahara S, Watanabe M, Izumi T. Tetrahedron Lett. 2008; 49: 3757
- 7d Kelland LR. Eur. J. Cancer 2005; 41: 971
- 7e Dexheimer TS, Sun D, Hurley LH. J. Am. Chem. Soc. 2006; 128: 5404
- 7f Kishioka S, Ko MC, Woods JH. Eur. J. Pharmacol. 2000; 397: 85
- 7g Richelson E, Souder T. Life Sci. 2000; 68: 29
- 7h Niu X, Yang B, Li Y, Fang S, Huang Z, Xie C, Ma C. Org. Biomol. Chem. 2013; 11: 4102
- 8a Desbene PL, Cherton JC, Leroux JP, Basselier JJ. Tetrahedron 1984; 40: 3539
- 8b Desbene PL, Cherton JC. Tetrahedron 1984; 40: 3559
- 9a Mouradzadegun A, Gheitasvand N. Phosphorus, Sulfur Silicon Relat. Elem. 2005; 180: 1385
- 9b Ganjali MR, Norouzi P, Emami M, Golmohamadi M, Pirelahi H, Mouradzadegun A. J. Chin. Chem. Soc. (Weinheim, Ger.) 2006; 53: 1209
- 9c Mouradzadegun A, Pirelahi H. J. Photochem. Photobiol., A 2001; 138: 203
- 9d Mouradzadegun A, Dianat Sh. J. Heterocycl. Chem. 2009; 46: 778
- 9e Mouradzadegun A, Ghasem Hezave F, Karimnia M. Phosphorus, Sulfur Silicon Relat. Elem. 2010; 185: 84
- 9f Mouradzadegun A, Abadast F. Tetrahedron Lett. 2013; 54: 2641
- 9g Kiasat AR, Mouradzadegun A, Elahi S, Fallah-Mehrjardi M. Chin. Chem. Lett. 2010; 21: 146
- 9h Mouradzadegun A, Abadast F. Synth. Commun. 2014; 44: 640
- 10 Tunstad LM, Tucker JA, Dalcanale E, Weiser J, Bryant JA, Sherman JC, Helgeson RC, Knobler CB, Cram DJ. J. Org. Chem. 1989; 54: 1305
- 11 Altshuler H, Ostapova E, Fedyaeva O, Sapozhnikova L, Altshuler O. Macromol. Symp. 2002; 181: 1
- 12 Jeevananda T, Yeon K.-H, Moon S.-H. J. Membr. Sci. 2006; 283: 201
- 13a Yilmaz A, Tabakci B, Akceylan E, Yilmaz M. Tetrahedron 2007; 63: 5000
- 13b Sayin S, Ozcan F, Yilmaz M. Desalination 2010; 262: 99
- 13c Budhathoki-Uprety J, Novak BM. Polymer 2010; 51: 2140
- 14a Chrobok A, Baj S, Pudlo W, Jarzebski A. Appl. Catal., A 2009; 366: 22
- 14b Qiu H, Mallik AK, Takafuji M, Liu X, Jiang S, Ihara H. Anal. Chim. Acta 2012; 738: 95
- 14c Rashinkar G, Kamble S, Kumbhar A, Salunkhe R. Catal. Commun. 2011; 12: 1442
- 15 Magonov SN, Reneker DH. Annu. Rev. Mater. Sci. 1997; 27: 175