"click" synthesis of nonsymmetrical bis(1,2,3-triazoles)

Organic Letters

Volumn 12, Issue 7, 2010, Pages 1584-1587

  Aizpurua, Jesus M ^a   Azcune, Itxaso ^a   Fratila, Raluca M ^b   Balentova, Eva ^a   Sagartzazu Aizpurua, Malaien ^a   Miranda, Jose I ^c  

^a UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

^b UNIVERSITY OF TWENTE   (Netherlands)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

TRIAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

MOLECULAR STRUCTURE; STEREOISOMERISM; TRIAZOLES;

EID: 77950233231     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1003127     Document Type: Article

References (35)

1. (a) Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057-3064.
2. (b) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596-2598.
3. For reviews, see; (a) Kolb, H. C.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2001, 40, 2004-2021.
4. (b) KoIb, H. C.; Sharpless, K. B. Drug Discovery Today 2003, 8, 1128-1137.
5. (c) Lutz, J.-F. Angew. Chem., Int. Ed. 2007, 46, 1018-1025.
6. (d) Moses, J. E.; Moorhouse, A. D. Chem. Soc. Rev. 2007, 36, 1249-1262.
7. (e) Lutz, J.-F.; Zarafshani, Z. Adv. Drug Delivery Rev. 2008, 60, 958-970.
8. (f) Moorhouse, A. D.; Moses, J. E. ChemMedChem 2008, 3, 715-723.
9. (g) Iron, G. C.; Pirali, T.; Billington, R. A.; Canonico, P. L.; Sorba, G.; Genazzani, A. A. Med. Res. Rev. 2008, 28, 278-308.
10. QSAR Comb. Sci. 2007, 26(11)is a special issue on click chemistry and its applications.
11. (a) McGlacken, G. P.; Bateman, L. M. Chem. Soc. Rev. 2009, 38, 2447-2464.
12. (b) Horton, D. A.; Bourne, G. T.; Smythe, M, L. Chem. Rev. 2003, 103, 893-930.
13. Angell, Y.; Burgess, K. Angew. Chem., Int. Ed. 2007, 46, 3649-3651.
14. (a) Monkowius, U.; Ritter, S.; König, B.; Zabel, M.; Yersin, H. Eur. J. Inorg. Chem. 2007, 459, 7-4606.
15. (b) Fletcher, J. T.; Bumgarner, B.; Engels, N. D.; Skoglund, D. A. Organometallics 2008, 27, 5430-5433.
16. A stepwise double-click strategy has been applied successfully to the preparation of α,ω-bis(l,2,3-triazolyl)peptides; see: (a) Aucagne, V.; Leigh, D. A. Org. Lett. 2006, 8, 4505-4507. For an iterative synthesis of triazolamers containing amino acids side chains, see:
17. (b) Angelo, N. G; Arora, P. S. J. Am Chem, Soc. 2005, 127, 17134-17135 and
18. J. Org. Chem. 2007, 72, 7963-7967. Oligomeric peptidomimetic compounds were synthesized from orthogonally protected l,4-disubstituted-l,2,3-triazoles, see:
19. (c) Montagnat, O. D.; Lessene, G.; Hughes, A. B. Tetrahedron Lett. 2006, 47, 6971-6974.
20. Tikhonova, L. G.; Serebryakova, E. S.; Proidakov, A. G.; Sokolova, I. E.; Vereshchagin, L. I. J. Org. Chem. USSR 1981, 17, 645-648.
21. Luu, T.; McDonald, R.; Tykwinski, R. R. Org. Lett. 2006, 8, 6035-6038.
22. (a) Reck, F.; Zhou, F.; Girardot, M..; Kern, G.; Eyermann, C. J.; Hales, N. J.; Ramsay, R. R.; Gravestock, M. B. J. Med. Chem. 2005, 48, 499-506.
23. (b) Josyula, V. P. V. N.; Boyer, F. E., Jr.; Kim, J.-Y. PCT Int. Appl. WO 2007/000644 Al.
24. Amegadzie, A. K.; Gardinier, K. M.; Hembre, E. J.; Hong, J. E.; Jungheim, L. N.; Muehl, B. S.; Remick, D. M.; Robertson, M. A.; Savin, K. A. PCT Int. Appl. WO 03/091227 Al.
25. Thibault, R. J.; Takizawa, K.; Lowenheilm, P.; Helms, B.; Mynar, J.; Fréchet, J. M. J.; Hawker, C. J. J. Am. Chem. Soc. 2006, 128, 12084-12085.
26. Takizawa, K.; Nulwala, H.; Thibault, R. J.; Lowenheilm, P.; Yoshinaga, K.; Wooley, K. L.; Hawker, C. J. J. Pohm. Sci., Part A 2008, 2897-2912.
27. (a) Ohira, S. Synth. Commun. 1989, 19, 561-564.
28. (b) Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521-522.
29. Tris[(l-benzyl-.l//-l,2,3-triazol-4-yl)m.ethyl]amine (TBTA): Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853-2855.
30. (a) Fiandanese, V.; Bottalico, D.; Marchese, G.; Punzi, A. Tetrahedron Lett. 2003, 44, 9087-9090.
31. (b) Holmes, A. B.; Jennings-White, C. L. D.; Schulthess, A. H.; Akinde, B.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1979, 840-842.
32. (c) Holmes, A. B.; Jones, G. E. Tetrahedron Lett. 1980, 21, 3111-3112.
33. 2O.
34. We found that desilylation of 9 with 0.4 equiv of TBAF (1 M, THF) in the presence of benzyl azide 6a and CuI/DIPEA led to the exclusive formation of symmetric bis-triazole la, whereas replacement of the copper(I) catalyst by the Sharpless system in aqueous organic medium resulted in the formation of 5-ethynyltriazole 5a as the major reaction product. Importantly, the one-pot sequential "click" cycloaddition of 9 with. azide 6a, followed by the addition of 6e or 6j, provided reaction mixtures containing, respectively, the unsymmetrically substituted bis-triazoles 4d and 4b as major products. Unfortunately, the chromatographic isolation of the products from symmetrical byproducts was laborious and afforded the desired compounds in modest vields. Chemical Reaction Repretation
35. Li, L.; Zhang, G.; Zhu, A.; Zhang, L. Org. Chem. 2008, 73, 3630-3633.