Thermal, non-catalyzed Huisgen cycloaddition for the preparation of 4,5-bis(trimethylsilyl)-1H-1,2,3-triazoles

Tetrahedron Letters

Volumn 54, Issue 3, 2013, Pages 272-276

  Brisbois, Ronald G ^a   Bergan, Alexandra M ^b   Ellison, Aubrey J ^a   Griffin, Percy Y ^a   Hackbarth, Kent C ^a   Larson, Steven R ^a  

^a MACALESTER COLLEGE   (United States)

^b Century Community College   (United States)

Author keywords

1,2,3 Triazole; Azide; Bis(trimethylsilyl)acetylene; Cycloaddition

Indexed keywords

4,5 BIS(TRIMETHYLSILYL)1H 1,2,3 TRIAZOLE DERIVATIVE; ACETYLENE DERIVATIVE; AZIDE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLOADDITION; DRUG SYNTHESIS; THERMAL HUISGEN CYCLOADDITION;

EID: 84871208916     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.11.019     Document Type: Article

References (60)

1. A.C. Tome R.C. Storr, T.L. Gilchrist, Science of Synthesis Vol. 13 2004 Thieme New York 415 601
2. V.P. Krivopalov, and O.P. Shkurko Russ. Chem. Rev. 74 2005 339
3. A. Michael J. Prakt. Chem. 48 1893 94 95
4. W.-Q. Fan, and A.R. Katritzky A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Comprehensive Heterocyclic Chemistry II Vol. 4 1996 Pergamon Press Oxford 1 126
5. H. Wamhoff A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry Vol. 5 1984 Pergamon Oxford 669
6. H. Dehne E. Schumann, Methoden der Organischen Chemie (Houben-Weyl) vol. E8d 1994 Thieme Stuttgart 305 405
7. H.C. Kolb, and K.B. Sharpless Drug Discovery Today 8 2003 1128 1137
8. R. Huisgen Pure Appl. Chem. 61 1989 613 628
9. R. Huisgen A. Padwa, 1,3-Dipolar Cycloaddition Chemistry 1984 Wiley New York
10. R. Huisgen, G. Szeimies, and L. Moebius Chem. Ber. 100 1967 2494 2507
11. R. Huisgen Angew. Chem., Int. Ed. Engl. 2 1963 565 598
12. R. Huisgen Angew. Chem., Int. Ed. Engl. 2 1963 633 645
13. M. Meldal, and C.W. Tornoe Chem. Rev. 108 2008 2952 3015
14. P. Wu, and V.V. Fokin Aldrich Chim. Acta 40 2007 7
15. V.V. Rostovtsev, L.G. Green, V.V. Fokin, and K.B. Sharpless Angew. Chem., Int. Ed. 41 2002 2596 2599
16. C.W. Tornoe, C. Christensen, and M. Meldal J. Org. Chem. 67 2002 3057 3064
17. H.C. Kolb, M.G. Finn, and K.B. Sharpless Angew. Chem., Int. Ed. 40 2001 2004 2021
18. C.W. Tornoe, and M. Meldal M. Lebl, R.A. Houghton, Peptides: The Wave of the Future 2001 American Peptide Society San Diego 263 264
19. L. Zhang, X. Chen, P. Xue, H.H.Y. Sun, I.D. Williams, K.B. Sharpless, V.V. Fokin, and G. Jia J. Am. Chem. Soc. 127 2005 15998 15999
20. B.C. Boren, S. Narayan, L.K. Rasmussen, L. Zhang, H. Zhao, Z. Lin, G. Jia, and V.V. Fokin J. Am. Chem. Soc. 130 2008 8923 8930
21. L.K. Rasmussen, B.C. Boren, and V.V. Fokin Org. Lett. 9 2007 5337 5339
22. A. Deiters, and P.G. Schultz Bioorg. Med. Chem. Lett. 15 2005 1521 1524
23. K.E. Beatty, F. Xie, Q. Wang, and D.A. Tirrell J. Am. Chem. Soc. 127 2005 14150 14151
24. A.E. Speers, G.C. Adam, and B.F. Cravatt J. Am. Chem. Soc. 125 2003 4686 4687
25. L. Kou, H. He, and C. Gao Nano-Micro Lett. 2 2010 177 183
26. L. Kou, H. He, and C. Gao Macromol. Rapid Commun. 29 2008 1073 1089
27. W.H. Binder, and R. Sachsenhofer Macromol. Rapid Commun. 28 2007 15 54
28. P.L. Golas, N.V. Tsarevsky, B.S. Sumerlin, and K. Matyjaszewski Macromolecules 39 2006 6451
29. R.J. Thibault, K. Takizawa, P. Lowenheilm, B. Helms, J.L. Mynar, J.M.J. Frechet, and C.J. Hawker J. Am. Chem. Soc. 128 2006 12084 12085
30. H. Struthers, T.L. Mindt, and R. Schibli Dalton Trans. 39 2010 675 696
31. M. Yano, C.C. Tong, M.E. Light, F.P. Schmidtchen, and P.A. Gale Org. Biomol. Chem. 8 2010 4356 4363
32. J.D. Crowley, P.H. Bandeen, and L.R. Hanton Polyhedron 29 2010 70 83
33. J.D. Crowley, and P.H. Bandeen Dalton Trans. 39 2010 612 623
34. M.L. Gower, and J.D. Crowley Dalton Trans. 39 2010 2371 2378
35. D. Urankar, B. Pinter, A. Pevec, F. De Proft, I. Turel, and J. Kosšmrlj Inorg. Chem. 49 2010 4820 4829
36. J.T. Fletcher, B.J. Bumgarner, N.D. Engels, and D.A. Skoglund Organometallics 27 2008 5430 5433
37. U. Monkowius, S. Ritter, B. Konig, M. Zabel, and H. Yersin Eur. J. Inorg. Chem. 29 2007 4597 4606
38. M. Sawa, T.-L. Hsu, T. Itoh, M. Sugiyama, S.R. Hanson, P.K. Vogt, and C.-H. Wong PNAS 103 2006 12371 12376
39. K. Sivakumar, F. Xie, B.N. Cash, S. Long, H.N. Barnhill, and Q. Wang Org. Lett. 6 2004 4603 4606
40. F. Kloss, U. Kohn, B.O. Jahn, M.D. Hager, H. Görls, and U.S. Schubert Chem. Asian J. 6 2011 2816 2824
41. C.R. Becer, R. Hoogenboom, and U.S. Schubert Angew. Chem., Int. Ed. 48 2009 4900 4908
42. E.M. Sletten, and C.R. Bertozzi Org. Lett. 10 2008 3097 3099
43. D.H. Ess, G.O. Jones, and K.N. Houk Org. Lett. 10 2008 1633 1636
44. S.T. Laughlin, J.M. Baskin, S.L. Amacher, and C.R. Bertozzi Science 320 2008 664 667
45. J.C. Jewett, and C.R. Bertozzi Chem. Soc. Rev. 39 2010 1272 1279
46. Brisbois, R. G.; Bergan, A. M.; Ke, X.; Larson, S. R. unpublished results.
47. X.-J. Wang, L. Zhang, D. Krishnamurthy, C.H. Senanayake, and P. Wipf Org. Lett. 12 2010 4632 4635
48. S. Mehta, and R.C. Larock J. Org. Chem. 75 2010 1652 1658
49. J. Huang, S.J.F. Macdonald, A.W.J. Cooper, G. Fisher, and J.P.A. Harrity Tetrahedron Lett. 50 2009 5539 5541
50. J. Huang, S.J.F. Macdonald, and J.P.A. Harrity Chem. Commun. 2009 436 438
51. We appreciate a reviewer's comment about this work raising the possibility that, given a synthetic investment to prepare bis(silacyclobutyl) acetylene derivatives, direct cross coupling on corresponding 4,5-bis(silacyclobutyl)-1,2,3-triazole products might obviate the need to first convert trimethylsilyl to halogen S.E. Denmark, and J.H.-C. Liu Angew. Chem., Int. Ed. 49 2010 2978 2986
52. S.E. Denmark, and C.R. Butler Chem. Commun. 2009 20 33
53. S.E. Denmark J. Org. Chem. 74 2009 2915 2927
54. S.E. Denmark, and R.F. Sweis Acc. Chem. Res. 35 2002 835 846
55. D.R. Armstrong, R.P. Davies, R. Haigh, M.A. Hendy, P.R. Raithby, R. Snaith, and A.E.H. Wheatley Eur. J. Inorg. Chem. 18 2003 3363 3375
56. G. Boche, J.C.W. Lohrenz, and F. Schubert Tetrahedron 50 1994 5889 5902
57. Willis, R. J.; Marlow, I. D. Eur. Pat. Appl. 1990, EP 400842 A1 19901205.
58. G. Michell, and C.W. Rees J. Chem. Soc., Perkin Trans. 1 1987 413 422
59. L. Birkofer, A. Ritter, and H. Uhlenbrauck Chem. Ber. 96 1963 3280 3288
60. W.C. Still, M. Kahn, and A. Mitra J. Org. Chem. 43 1978 2923 2925