Synthesis of macrocycles containing tetrazole units-potential metal complexation sites

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 61, Issue 1-2, 2008, Pages 1-10

  McGinley, John ^a   Fleming, Adrienne ^b  

^a NATIONAL UNIVERSITY OF IRELAND   (Ireland)

^b DUBLIN INSTITUTE OF TECHNOLOGY   (Ireland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 44149098909     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-007-9396-y     Document Type: Article

References (61)

1. Vigato, P.A., Tamburini, S.: The challenge of cyclic and acyclic schiff bases and related derivatives. Coord. Chem. Rev. 248, 1717-2128 (2004)
2. Fenton, D.E., Vigato, P.A.: Macrocyclic schiff base complexes of lanthanides and actinides. Chem. Soc. Rev. 17, 69-90 (1988)
3. Vigato, P.A., Tamburini, S., Fenton, D.E.: The activation of small molecules by dinuclear complexes of copper and other metals. Coord. Chem. Rev. 106, 25-170 (1990)
4. Menif, R., Martell, A.E., Squattrito, P.J., Clearfield, A.: New hexaaza macrocyclic binucleating ligands. Oxygen insertion with a dicopper(I) schiff base macrocyclic complex. Inorg. Chem. 29, 4723-4729 (1990)
5. Collinson, S.R., Fenton, D.E.: Metal complexes of bibracchial schiff base macrocycles. Coord. Chem. Rev. 148, 19-40 (1996)
6. Okawa, H., Furutachi, H., Fenton, D.E.: Heterodinuclear metal complexes of phenol-based compartmental macrocycles. Coord. Chem. Rev. 174, 51-75 (1998)
7. Amendola, V., Fabbrizzi, L., Mangano, C., Pallavicini, P., Poggi, A., Taglietti, A.: Anion recognition by dimetallic cryptates. Coord. Chem. Rev. 219-221, 821-837 (2001)
8. Brooker, S.: Complexes of thiophenolate-containing schiff-base macrocycles and their amine analogues. Coord. Chem. Rev. 222, 33-56 (2001)
9. 4 topological 2-D rare-earth coordination polymers from a flexible tripodal acid with additional amide groups. Inorg. Chem. 46, 8451-8453 (2007) and references therein
10. See, for example, Al-Rasbi, N.K., Adams, H., Harding, L.P., Ward, M.D.: Coordination behaviour of bis-terdentate N-donor ligands: double- and single-stranded helicates, mesocates and cyclic oligomers. Eur. J. Inorg. Chem. 4770-4780 (2007) and references therein
11. See, for example, (a) Huang, X.C., Lin, Y.Y., Zhang, J.P., Chen, X.M.: Ligand-directed strategy for zeolite-type metal-organic frameworks: zinc(II) imidazolates with unusual zeolitic topologies. Angew. Chem. Int. Ed. 45, 1557-1559 (2006);
12. (b) Sun, J., Weng, L., Zhou, Y., Chen, J., Chen, Z., Liu, Z., Zhao, D.: QMOF-1 and QMOF-2: three-dimensional metal-organic open frameworks with a quartzlike topology. Angew. Chem. Int. Ed. 41, 4471-4473 (2002);
13. 2] (M = Co or Ni). J. Chem. Soc. Dalton Trans. 2977-2986 (1999)
14. Hammes, B.S., Ramos-Maldonado, D., Yap, G.P.A., Rheingold, A.L., Young, V.G. Jr., Borovik, A.S.: The use of C3-symmetric tripodal ligands in crystal engineering. Coord. Chem. Rev. 174, 241-253 (1998)
15. See, for example, (a) Hannon, M.J., Childs, L.J.: Helices and helicates: beautiful supramolecular motifs with emerging application. Supramol. Chem. 16, 7-22 (2004);
16. (b) Albrecht, M.: "Let's twist again"-double-stranded, triple-stranded and circular helicates. Chem. Rev. 101, 3457-3497 (2001);
17. (c) Harding, L.P., Jeffrey, J.C., Riis-Johannessen, T., Rice, C.R., Zeng, Z.: Anion control of ligand self-recognition in a triple helical way. Chem. Commun. 654-655 (2004);
18. (d) Harding, L.P., Jeffrey, J.C., Riis-Johannessen, T., Rice, C.R., Zeng, Z.: Anion control of the formation of geometric isomers in a triple helical way. Dalton Trans. 2396-2397 (2004);
19. (e) Jeffrey, J.C., Riis-Johannessen, T., Anderson, C.J., Adams, C.J., Robinson, A., Argent, S.P., Ward, M.D., Rice, C.R.: Localization and delocalization in a mixed-valence dicopper helicate. Inorg. Chem. 46, 2417-2426 (2007);
20. (f) Nitschke, J.R.: Construction, substitution, and sorting of metallo-organic structures via subcomponent self-assembly. Acc. Chem. Res. 40, 103-112 (2007)
21. See, for example, (a) Aly, A.A.M., Vatsadze, S.Z., Chernikov, A.V., Walfort, B., Rueffer, T., Lang, H.: A binuclear silver(I) perchlorate macrocycle based on 2,5-bis[(E)-(3-pyridyl)methylene]cyclopentanone: crystal structure and solution behaviour. Polyhedron 26, 3925-3929 (2007);
22. (b) Spitler, E.L., McClintock, S.P., Haley, M.M.: Dynamic proton-induced emission switching in donor-functionalized dehydrobenzopyrid[15]annulenes. J. Org. Chem. 72, 6692-6699 (2007);
23. (c) Katayev, E.A., Ustynuk, Y.A., Lynch, V.M., Sessler, J.L.: Mono-palladium(II) complexes of diamidopyridine-dipyrromethane hybrid macrocycles. Chem. Commun. 4682-4684 (2006);
24. (d) Li, F., Delgado, R., Drew, M.G.B., Felix, V.: Dioxadiaza- and trioxadiaza-macrocycles containing one benzofuran unit selective for cadnium. Dalton Trans. 5396-5403 (2006);
25. 3-donor macrocycle for enhanced silver(I) discrimination. Dalton Trans. 5115-5117 (2006);
26. (f) Habermehl, N.C., Mohr, F., Eisler, D.J., Jennings, M.C., Puddephatt, R.J.: Organogold(I) macrocycles and [2]catenanes containing pyridyl and bipyridyl substituents-organometallic catenanes as ligands. Can. J. Chem. 84, 111-123 (2006);
27. (g) Koschabek, R., Gleiter, R., Rominger, F.: Synthesis and properties of cryptands with a thioether bridge and π-donors-silver(I) and copper(I)-complexes. Eur. J. Org. Chem. 609-620 (2006)
28. Ried, W., Tsiotis, G.: Synthesis of new cyclophanes from pyrazinedicarbonitriles. Chem. Ztg. 112, 385-386 (1988)
29. Ried, W., Aboul-Fetouh, S.: Synthesis of substituted heterocyclic cyclophanes. Tetrahedron. 44, 3399-3404 (1988)
30. Ried, W., Lee, C., Bats, J.W.: New heterocyclic phanes from 2,3-bis(5-tetrazolyl)pyrazines and α,ω-dibromoalkanes. Liebigs Ann. Chem. 497-500 (1989)
31. Ried, W., Laoutidis, J.: Synthesis of new, heterocyclic phanes from 1,2,3-triazolo-4,5-dicarbonitrile. Chem. Ztg. 113, 384-385 (1989)
32. Butler, R.N., Quinn, F., Welke, B.: Tetratetrazole macrocycles. J. Chem. Soc. Chem. Commun. 1481-1482 (1992)
33. Butler, R.N., Ní Bhrádaigh, E.: Tetratetrazolophanes. J. Chem. Res. (S). 148-149 (1994)
34. Butler, R.N., Fleming, A.F.M.: meta-Benzenotetratetrazolophanes. J. Heterocycl. Chem. 34, 691-693 (1997)
35. Bethel, P.A., Hill, M.S., Mahon, M.F., Molloy, K.C.: Reactions of organotin tetrazoles: synthesis of functionalised poly-tetrazoles. J. Chem. Soc. Perkin Trans. 1, 3507-3514 (1999)
36. Zubarev, V.Y., Trifonov, R.E., Filichev, V.V., Ostrovskii, V.A., Abell, A.D., Edmonds, M.K.: Synthesis, X-ray and conformational studies of novel tetrazole-containing macrocycles: 4,13-dioxa-1,7,8,9,17,18,19,20- octaazatricyclo[14.2.1.17,10]icosa-8,10(20),16(19),17-tetraene and 4,14-dioxa-1,7,8,9,10,18,19,20-octaazatricyclo[15.2.1.07,10]icosa-8,10,17(20), 18-tetraene. J. Chem. Soc. Perkin Trans. 2, 417-421 (2001)
37. Butler, R.N., McGinley, J.M.G., Mahon, M.F., Molloy, K.C., Ní Bhrádaigh, E.P.: Diorthobenzenotetra(5',2'-tetrazolo)[5'-(2)-(2'-(6)] cyclophane. Acta Cryst. E57, o195-o197 (2001)
38. See, for example, (a) Butler, R.N.: In: Katritzky, A.R., Rees, C.W., Scriven, E.F.V. (eds) Comprehensive Heterocyclic Chemistry, vol 4, Permagon, Oxford (1996);
39. (b) Herr, R.J.: 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods. Bioorg. Med. Chem. 10, 3379-3393 (2002);
40. (c) Ostrovskii, V.A., Pevzner, M.S., Kofman, T.P., Shcherbinin, M.B., Tselinskii, I.V.: Energetic 1,2,4-triazoles and tetrazoles synthesis, structure and properties. Targets Heterocycl Syst. 3, 467-526 (1999)
41. Zych, A.J., Herr, R.J.: Tetrazoles as carboxylic acid bioisosteres in drug discovery. PharmaChem. 6, 21-24 (2007)
42. IUPAC, Commission on Nomenclature of Organic Chemistry: A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993), Blackwell Scientific (1993)
43. See, for example, (a) Kaden, T.A.: Dinuclear metal complexes of bis-macrocycles. Coord. Chem. Rev. 190-192, 371-389 (1999);
44. (b) Tarrago, T., Marzin, C., Najimi, O., Pellegrin, V.: New tetraheterocyclic macrocycles containing triazole, pyrazole, pyridine, and/or furan subunits. Synthesis and cation binding properties. J. Org. Chem. 55, 420-425 (1990);
45. (c) Newkome, G.R., Sauer, J.D., Roper, J.M., Hager, D.C.: Construction of synthetic macrocyclic compounds possessing subheterocyclic rings, specifically pyridine, furan and thiophene. Chem. Rev. 77, 513-597 (1977)
46. Hill. M., Mahon, M.F., McGinley, J., Molloy, K.C.: New supramolecular architectures based on polyfunctional organotin tetrazoles: synthesis and characterisation of phenylene-bridged bis(organotin tetrazoles). J. Chem. Soc. Dalton Trans. 835-845 (1996)
47. 6. J. Chem. Soc. Dalton Trans. 847-852 (1996)
48. Hill. M., Mahon, M.F., Molloy, K.C.: Tris(triorganostannyltetrazoles): synthesis and supramolecular structures. J. Chem. Soc. Dalton Trans. 1875-1865 (1996)
49. Bhandari, S., Mahon, M.F., Molloy, K.C.: Synthesis and supramolecular architectures of tetrakis(triorganostannyltetrazoles), including the crystal structure of hydrated 1,2,4,5- tetrakis(triethylstannyltetrazolyl)benzene. J. Chem. Soc. Dalton Trans. 1951-1956 (1999)
50. Bhandari, S., Frost, C.G., Hague, C.E., Mahon, M.F., Molloy, K.C.: Synthesis of functionalised (triorganostannyl)tetrazoles: supramolecular structures of n-[2- (triorganostannyl)tetrazol-5-yl]pyridine (n = 2, 3 or 4). Dalton Trans. 663-669 (2000)
51. Bhandari, S., Mahon, M.F., Molloy, K.C., Palmer, J.S., Sayers, S.F.: Thallium(I)- and organothallium(III)-substituted mono-, bis- and tris-tetrazoles: synthesis and supramolecular structures. Dalton Trans. 1053-1060 (2000)
52. Bond, A.D., Fleming, A., Kelleher, F., McGinley J., Prajapati, V.: Reactions of 1,4-bis(tetrazole)benzenes: formation of long chain alkyl halides. Tetrahedron 62, 9577-9581 (2006)
53. Bond, A.D., Fleming, A., Kelleher, F., McGinley, J., Prajapati, V., Skovsgaard, S.: Synthesis and characterisation of tetra-tetrazole macrocycles. Tetrahedron 63, 6835-6842 (2006)
54. Fleming, A., Kelleher, F., Mahon, M.F., McGinley, J., Prajapati, V.: Reactions of bis(tetrazole)phenylenes. Surprising formation of vinyl compounds from alkyl halides. Tetrahedron 61, 7002-7011 (2005)
55. Prajapati, V.: PhD thesis. Higher Education and Training Awards Council, Ireland (2007)
56. Szumna, A., Jurczak, J.: A new macrocyclic polylactam-type neutral receptor for anions-structural aspects of anion recognition. Eur. J. org. Chem. 4031-4039 (2001)
57. Chmielewski, M., Jurczak, J.: Size complementarity in anion recognition by neutral macrocyclic tetraamides. Tetrahedron Lett. 45, 6007-6010 (2004)
58. Duncia, J.V., Pierce, M.E., Santella, J.B.: Three synthetic routes to a sterically hindered tetrazole. A new one-step conversion of an amide into a tetrazole. J. Org. Chem. 56, 2395-2400 (1991)
59. C: 26.8, 28.8, 29.0, 40.2, 127.5, 129.0, 130.5, 134.3, 166.9; HRMS (EI) Calc. 549.3441, Found 549.3428
60. C: 24.0, 24.9, 26.3, 27.6, 27.7, 28.6, 40.0, 47.9, 122.7, 125.4, 127.5, 130.3, 131.1, 131.9, 136.7, 153.2, 167.6; HRMS (EI) Calc. 593.3074, Found 593.3080
61. Thomas, E.W.: The conversion of secondary amides to tetrazoles with trifluoromethanesulfonic anhydride and sodium azide. Synthesis 767-768 (1993)