Synthetic Protocols towards Selenacalix[3]triazines

Joice Thomas; Wim Van Rossom; Kristof Van Hecke; Luc Van Meervelt; Mario Smet; WimWouter DehaenMaes

doi:10.1055/s-0032-1318265

Synthesis, Table of Contents

Synthesis 2013; 45(6): 734-742
DOI: 10.1055/s-0032-1318265

paper

Synthetic Protocols towards Selenacalix[3]triazines

Joice Thomas

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium Fax: +32(16)327990 Email: wim.dehaen@chem.kuleuven.be

,

Wim Van Rossom

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium Fax: +32(16)327990 Email: wim.dehaen@chem.kuleuven.be

,

Kristof Van Hecke

^bBiomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

^cDepartment of Inorganic and Physical Chemistry, Ghent University, Krijgslaan 281, Building S3, 9000 Ghent, Belgium

,

Luc Van Meervelt

^bBiomolecular Architecture, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

,

Mario Smet

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium Fax: +32(16)327990 Email: wim.dehaen@chem.kuleuven.be

,

Wim Dehaen*

^aMolecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium Fax: +32(16)327990 Email: wim.dehaen@chem.kuleuven.be

^dDesign & Synthesis of Organic Semiconductors (DSOS), Institute for Materials Research (IMO-IMOMEC), Hasselt University, Universitaire Campus, Agoralaan 1 – Building D, 3590 Diepenbeek, Belgium Email: wouter.maes@uhasselt.be

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Abstract

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Abstract

Selenium-bridged heteracalixarenes were synthesized by convenient one-pot S_NAr reactions starting from variously 2-substituted 4,6-dichloro-1,3,5-triazine building blocks. Reactions of these precursors with sodium hydroselenide afforded the selenacalix[3]triazines as the only macrocyclic products. Yields of the cyclotrimers were significantly increased by optimization of the macrocyclization conditions, the optimum parameters being dependent on the triazine functionalization pattern. X-ray diffraction studies allowed unambiguous identification of the structures and comparison with the solid-state features of analogous heteracalixarenes.

Key words

(hetera)calixarenes - macrocycles - selenium - 1,3,5-triazines - substituent effects

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References

References

1a Calixarenes 2001 . Asfari Z, Böhmer V, Harrowfield J, Vicens J. Kluwer Academic Publishers; Dordrecht (The Netherlands): 2001
1b Gutsche CD. Calixarenes: An Introduction . 2nd ed., Stoddart JF. Royal Society of Chemistry; Cambridge: 2008

2 We prefer the term heteracalixarenes to distinguish this class of heteroatom-bridged macrocycles from heterocalixarenes, the heterocyclic analogues of classical C-bridged calixarenes, e.g., calixpyrroles.

Heteracalixarene review articles:

3a König B, Fonseca MH. Eur. J. Inorg. Chem. 2000; 2303
3b Lhotak P. Eur. J. Org. Chem. 2004; 1675
3c Morohashi N, Narumi F, Iki N, Hattori T, Miyano S. Chem. Rev. 2006; 106: 5291
3d Kajiwara T, Iki N, Yamashita M. Coord. Chem. Rev. 2007; 251: 1734
3e Tsue H, Ishibashi K, Tamura R In Heterocyclic Supramolecules I . Vol. 17. Matsumoto K. Topics in Heterocyclic Chemistry; Springer; Heidelberg: 2008: 73-96
3f Maes W, Dehaen W. Chem. Soc. Rev. 2008; 37: 2393
3g Wang M.-X. Chem. Commun. 2008; 4541
3h Zuo C.-S, Wiest O, Wu Y.-D. J. Phys. Org. Chem. 2011; 24: 1157
3i Wang M.-X. Acc. Chem. Res. 2012; 45: 182

Thiacalixarenes:

4a Kajiwara T, Iki N, Yamashita M. Coord. Chem. Rev. 2007; 251: 1734
4b Buccella D, Parkin G. J. Am. Chem. Soc. 2008; 130: 8617
4c Kozlova MN, Ferlay S, Kyritsakas N, Hosseini MW, Solovieva SE, Antipin IS, Konovalov AI. Chem. Commun. 2009; 2514
4d Yamada M, Shimakawa Y, Kondo Y, Hamada F. CrystEngComm 2010; 12: 1311

Azacalixarenes:

5a Wang M.-X, Zhang X.-H, Zheng Q.-Y. Angew. Chem. Int. Ed. 2004; 43: 838
5b Zhang E.-X, Wang D.-X, Zheng Q.-Y, Wang M.-X. Org. Lett. 2008; 10: 2565
5c Tsue H, Ishibashi K, Tokita S, Takahashi H, Matsui K, Tamura R. Chem. Eur. J. 2008; 14: 6125
5d Lawson KV, Barton AC, Spence JD. Org. Lett. 2009; 11: 895
5e Katz JL, Tschaen BA. Org. Lett. 2010; 12: 4300
5f Wang L.-X, Wang D.-X, Huang Z.-T, Wang M.-X. J. Org. Chem. 2010; 75: 741
5g Xue M, Chen C.-F. Chem. Commun. 2011; 47: 2318
5h Touil M, Elhabiri M, Lachkar M, Siri O. Eur. J. Org. Chem. 2011; 1914
5i Vicente AI, Caio JM, Sardinha J, Moiteiro C, Delgado R, Félix V. Tetrahedron 2012; 68: 670
5j Tsue H, Takahashi H, Ishibashi K, Inoue R, Shimizu S, Takahashi D, Tamura R. CrystEngComm 2012; 14: 1021
5k Yi Y, Fa S, Cao W, Zeng L, Wang M, Xu H, Zhang X. Chem. Commun. 2012; 48: 7495
5l Wu J.-C, Zhao L, Wang D.-X, Wang M.-X. Inorg. Chem. 2012; 51: 3860

Oxacalixarenes:

6a Wang M.-X, Yang H.-B. J. Am. Chem. Soc. 2004; 126: 15412
6b Wang D.-X, Zheng Q.-Y, Wang Q.-Q, Wang M.-X. Angew. Chem. Int. Ed. 2008; 47: 7485
6c Ma M.-L, Li X.-Y, Wen K. J. Am. Chem. Soc. 2009; 131: 8338
6d Wang Q.-Q, Wang D.-X, Yang H.-B, Huang Z.-T, Wang M.-X. Chem. Eur. J. 2010; 16: 7265
6e Wang D.-X, Wang Q.-Q, Han Y, Wang Y, Huang Z.-T, Wang M.-X. Chem. Eur. J. 2010; 16: 13053
6f Hu S.-Z, Chen C.-F. Chem. Commun. 2010; 46: 4199
6g Alberto ME, Mazzone G, Russo N, Sicilia E. Chem. Commun. 2010; 46: 5894
6h Chen Y, Wang D.-X, Huang Z.-T, Wang M.-X. Chem. Commun. 2011; 47: 8112
6i Gargiulli C, Gattuso G, Notti A, Pappalardo S, Parisi MF, Puntoriero F. Tetrahedron Lett. 2012; 53: 616

7a Mugesh G, du Mont W.-W, Sies H. Chem. Rev. 2001; 101: 2125
7b Björkhem-Bergman L, Torndal U.-B, Eken S, Nystrom C, Capitanio A, Larsen EH, Björnstedt M, Eriksson LC. Carcinogenesis 2005; 26: 125
7c Nogueira CW, Zeni G, Rocha JB. T. Chem. Rev. 2004; 104: 6255
7d Roy G, Mugesh G. J. Am. Chem. Soc. 2005; 127: 15207
7e Mukherjee JA, Zade SS, Singh HB, Sunoj RB. Chem. Rev. 2010; 110: 4357

GPx mimics:

8a Back TG, Moussa Z, Parvez M. Angew. Chem. Int. Ed. 2004; 43: 1268
8b Dong Z, Liu J, Mao S, Huang X, Yang B, Ren X, Luo G, Shen J. J. Am. Chem. Soc. 2004; 126: 16395
8c Xu H, Gao J, Wang Y, Wang Z, Smet M, Dehaen W, Zhang X. Chem. Commun. 2006; 796
8d Bhabak KP, Mugesh G. Acc. Chem. Res. 2010; 43: 1408
8e Fu Y, Chen J, Van Oosterwijck C, Zhang X, Dehaen W, Smet M. Macromol. Rapid Commun. 2012; 33: 798
8f Soares LC, Alberto EE, Schwab RS, Taube PS, Nascimento V, Rodrigues OE. D, Braga AL. Org. Biomol. Chem. 2012; 10: 6595

9a Levason W, Orchard SD, Reid G. Coord. Chem. Rev. 2002; 225: 159
9b Shimizu T, Kawaguchi M, Tsuchiya T, Hirabayashi K, Kamigata N. Org. Lett. 2003; 5: 1443
9c Shimizu T, Kawaguchi M, Tsuchiya T, Hirabayashi K, Kamigata N. J. Org. Chem. 2005; 70: 5036
9d Levason W, Manning JM, Pawelzyk P, Reid G. Eur. J. Inorg. Chem. 2006; 4380
9e Panda S, Zade SS, Panda A, Singh HB, Butcher RJ. J. Organomet. Chem. 2006; 691: 2793
9f Hua G, Li Y, Slawin AM. Z, Woollins JD. Angew. Chem. Int. Ed. 2008; 47: 2857
9g Levason W, Manning JM, Reid G, Tuggey M, Webster M. Dalton Trans. 2009; 4569
9h Panda A. Coord. Chem. Rev. 2009; 253: 1056
9i Jing S, Morley CP, Gu C.-Y, Di Vaira M. Dalton Trans. 2010; 39: 8812
9j Panda A, Panda S, Srivastava K, Singh HB. Inorg. Chim. Acta 2011; 372: 17

Homoselenacalixarenes:

10a Thomas J, Maes W, Robeyns K, Ovaere M, Van Meervelt L, Smet M, Dehaen W. Org. Lett. 2009; 11: 3040
10b Thomas J, Dobrzanska L, Van Hecke K, Sonawane MP, Robeyns K, Van Meervelt L, Wozniak K, Smet M, Maes W, Dehaen W. Org. Biomol. Chem. 2012; 10: 6526

11a Maes W, Van Rossom W, Van Hecke K, Van Meervelt L, Dehaen W. Org. Lett. 2006; 8: 4161
11b Van Rossom W, Maes W, Kishore L, Ovaere M, Van Meervelt L, Dehaen W. Org. Lett. 2008; 10: 585
11c Maes W, Dehaen W. Pol. J. Chem. 2008; 82: 1145
11d Van Rossom W, Ovaere M, Van Meervelt L, Dehaen W, Maes W. Org. Lett. 2009; 11: 1681
11e Van Rossom W, Kishore L, Robeyns K, Van Meervelt L, Dehaen W, Maes W. Eur. J. Org. Chem. 2010; 4122
11f Van Rossom W, Kundrat O, Ngo TH, Lhotak P, Dehaen W, Maes W. Tetrahedron Lett. 2010; 51: 2423
11g Van Rossom W, Robeyns K, Ovaere M, Van Meervelt L, Dehaen W, Maes W. Org. Lett. 2011; 13: 126
11h Van Rossom W, Caers J, Robeyns K, Van Meervelt L, Maes W, Dehaen W. J. Org. Chem. 2012; 77: 2791

12 A short communication on the synthesis and host-guest chemistry of these materials has very recently been published: Thomas J, Van Rossom W, Van Hecke K, Van Meervelt L, Smet M, Maes W, Dehaen W. Chem. Commun. 2012; 48: 43

13a Verheyde B, Maes W, Dehaen W. Mater. Sci. Eng. C 2001; 18: 243
13b Steffensen MB, Simanek EE. Angew. Chem. Int. Ed. 2004; 43: 5178
13c Blotny G. Tetrahedron 2006; 62: 9507
13d Rothmann MM, Haneder S, Da Como E, Lennartz C, Schildknecht C, Stroghriegl P. Chem. Mater. 2010; 22: 2403

Heteracalix[3]arenes:

14a Reistad KR, Groth P, Lie R, Undheim K. J. Chem. Soc., Chem. Commun. 1972; 1059
14b Sergeev VA, Ovchinnikov YE, Nedelkin VI, Astankov AV, Andrianova OB, Shklover VE, Zamaev IA, Struchkov YT. Izv. Akad. Nauk SSSR, Ser. Khim., Engl. Transl. 1989; 1440
14c Mascal M, Richardson JL, Blake JA, Li W. Tetrahedron Lett. 1997; 38: 7639
14d Ito A, Ono Y, Tanaka K. J. Org. Chem. 1999; 64: 8236
14e Tanaka R, Yano T, Nishioka T, Nakajo K, Breedlove BK, Kimura K, Kinoshita I, Isobe K. Chem. Commun. 2002; 1686
14f Kinoshita I, Hamazawa A, Nishioka T, Adachi H, Suzuki H, Miyazaki Y, Tsuboyama A, Okada S, Hoshino M. Chem. Phys. Lett. 2003; 371: 451
14g Nishioka T, Onishi Y, Nakajo K, Guo-Xin J, Tanaka R, Kinoshita I. Dalton Trans. 2005; 2130
14h Suzuki Y, Yanagi T, Kanbara T, Yamamoto T. Synlett 2005; 263
14i Hamazawa RT, Nishioka T, Kinoshita I, Takui T, Santo R, Ichimura A. Dalton Trans. 2006; 1374
14j Kanbara T, Suzuki Y, Yamamoto T. Eur. J. Org. Chem. 2006; 3314
14k Tsukahara Y, Hirotsu M, Hattori S, Usuki Y, Kinoshita I. Chem. Lett. 2008; 37: 452
14l Uchida N, Taketoshi A, Kuwabara J, Yamamoto T, Inoue Y, Watanabe Y, Kanbara T. Org. Lett. 2010; 12: 5242

15 Rowan SJ, Cantrill SJ, Cousins GR. L, Sanders JK. M, Stoddart JF. Angew. Chem. Int. Ed. 2002; 41: 898
16 The crystallographic features of selenacalix[3]triazine 2d (R = NEt₂) are reported in our previous communication (ref. 12).
17 The related azacalix[3]pyridine (R = p-tolyl) macrocycle reported by Yamamoto and co-workers adopts a triangular shape (approximate C _S symmetry) with one pyridine ring facing an opposite direction to minimize electrostatic repulsion between the pyridine lone pairs inside the cavity (ref. 14h).
18 For an overview of nonbonding interactions involving Se atoms: Coles MP. Curr. Org. Chem. 2006; 10: 1993
19 Gottlieb HE, Kotlyar V, Nudelman A. J. Org. Chem. 1997; 62: 7512
20 Duddeck H. Prog. Nucl. Magn. Reson. Spectrosc. 1995; 27: 1
21 Hintermann L, Xiao L, Labonne A. Angew. Chem. Int. Ed. 2008; 47: 8246
22 Götz RJ, Robertazzi A, Mutikainen I, Turpeinen U, Gamez P, Reedijk J. Chem. Commun. 2008; 3384
23 Hermon T, Tshuva EY. J. Org. Chem. 2008; 73: 5953
24 Bruun L, Koch C, Jakobsen MH, Pedersen B, Christiansen M, Aamand J. Anal. Chim. Acta 2001; 436: 87
25 Mochowski J, Syper L. Sodium Hydrogen Selenide . In Encyclopedia of Reagents for Organic Synthesis . Paquette LA. Wiley; New York: 2001: rs079
26 Klayman DL, Griffin TS. J. Am. Chem. Soc. 1973; 95: 197
27 SAINT, Manual Version 5/6.0 . Bruker Analytical X-ray Systems Inc; Madison: 1997
28 SHELXTL-NT, Manual Version 5.1 . Bruker Analytical X-ray Systems Inc; Madison: 1997
29 CCDC 808716 contains the supplementary crystallographic data for this paper (compound 2c) and can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif.

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