Fimctlonalized tetrazoles from cyanogen azide with secondary amines

European Journal of Organic Chemistry

Volumn , Issue 21, 2009, Pages 3573-3578

  Joo, Young Hyuk ^a   Shreeve, Jean'ne M ^a  

^a UNIVERSITY OF IDAHO   (United States)

Author keywords

Azides; Cyclization; Nitrogen heterocycles; Tetrazole

Indexed keywords

EID: 67650760387     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc200900389     Document Type: Article

References (51)

1. R. N. Butler, in: Comprehensive Heterocyclic. Chemistry II (Eds.: A. R. Katritzky, C. W. Rees, E. F. V. Scriven). Pergamon. Oxford, U. K., 1996, vol. 4.
2. a) R. P. Singh, R. D. Verma, D. T. Meshri, J. M. Shreeve, Angew. Chem. Int. Ed. 2006, 45, 3584-3601;
3. b) G. Steinhauser, T. M. Klapötke, Angew. Chem. Int. Ed. 2008, 47, 3330-3347.
4. G.-H. Tao. Y. Guo, Y.-H. Joo, B. Twamley, J. M. Shreeve, J. Mater. Chem. 2008, 18, 5524-5530.
5. a) H. C. Kolb. M. G. Finn, K. B. Sharpless, Angew. Chem. Int. Ed. 2001, 40, 2004-2021;
6. b) Z. P. Demko, K. B. Sharpless, J. Org. Chem. 2001, 66, 7945-7950;
7. c) F. Himo, Z. P. Demko, L. Noodleman, K. B. Sharpless, J. Am. Chem. Soc. 2003, 125, 9983-9937;
8. d) Z. P. Demko, K. B. Sharpless, Angew. Chem. Int. Ed. 2002, 41, 2110-2113;
9. e) Z. P. Demko, K. B. Sharpless, Org. Lett. 2002, 4, 2525-2527;
10. f) O. G. Mancheno, C. Bolm, Org. Lett. 2007, 9, 2951-2954;
11. g) J.-J. Shie, J.-M. Fang, J. Org. Chem. 2003, 68, 1158-1160.
12. a) 1 T. Kuethe, A. Wong, C. Qu, 1 Smitrovich, I. W. Davies, D. L. Hughes, J. Org. Chem. 2005, 70, 2555-2567;
13. b) M. C. V. Zandt, M. L. Jones, D. E. Gunn, L. S. Geraci, J. H. Jones, D. R. Sawicki, J. Sredy, J. L. Jacot, A. T. Dicioccio, T. Petrova, A. Mitschler, A. D. Podjarny, J. Med. Chem. 2005, 48, 3141-3152;
14. c) N. Mekni, A. Baklouti, J. Fluorine Chem. 2008, 129, 1073-1075.
15. a) F. D. Marsh, M. E. Hermes, J. Am. Chem. Soc. 1964, 86, 4506-4507:
16. b) F. D. Marsh, J. Org. Chem. 1972, 37, 2966-2969;
17. c) J. E. McMurry, A. P. Coppolino, J. Org. Chem. 1973, 38, 2821-2827:
18. d) K. Banert, Y.-H. Joo, T. Rüffer, B. Walfort, H. Lang, Angew. Chem. Int. Ed. 2007, 46, 1168-1171.
19. a) Y.-H. Joo, J. M. Shreeve, Org. Lett. 2008, 10, 4665-4667;
20. b) Y.-H. Joo, B. Twamley, S. Garg, J. M. Shreeve, Angew. Chem. Int. Ed. 2008, 47, 6236-6239.
21. W. P. Norris, R. A. Henry, J. Org. Chem. 1964, 29, 650-660.
22. a) Y.-H. Joo, J. M. Shreeve, Angew. Chem. Int. Ed. 2009, 48, 564-567;
23. b) Y.-H. Joo, J. M. Shreeve, Chem. Eur. J. 2009, 15, 3198-3203.
24. a) T. M. Klapotke, J. Stierstorfer, J. Am. Chem. Soc. 2009, 131, 1122-1134;
25. b) J. Stierstorfer, T. M. Klapötke, A. Hammerl, R. I). Chapman, Z, Anorg. Allg. Chem. 2008, 634, 1051-1057;
26. c) T. Abe, G.-H. Tao, Y.-H. Joo, Y. Huang, B. Twamley, J. M. Shreeve, Angew. Chem. Int. Ed. 2008, 47, 7087-7090;
27. d) T. Abe, Y.-H. Joo, G.-H. Tao, B. Twamley, J. M. Shreeve, Chem. Eur. J. 2009, 15, 4102-4110;
28. e) P. Buzek, T. M. Klapotke, P. v. R. Schleyer, J. C. Tornieporth-Oetting, P. S. White, Angew. Chem. Int. Ed. Engl. 1993, 32, 275-277;
29. f) M. Hargittai, I. C. Tornieporth-Oetting, T. M. Klapotke, M. Kolonits, J. Hargittai, Angew. Chem. Int. Ed. Engl. 1993, 32, 759-761;
30. g) A. Schulz, J. C. Tornieporth-Oetting, T. M. Klapötke, Angew. Chem. Int. Ed. Engl 1993, 32, 1610-1612.
31. a) W. G. Finnegan, R. A. Henry, E. Lieber, J. Org. Chem. 1953, 18, 779-791;
32. b) A. J. Papa, J. Org. Chem. 1966, 31, 1430-1433;
33. c) C. P. Bergstrom, C. P. Sloan, H. H. Wang, M. F. Parker, D. W. Smith, M. Zheng, S. B. Hansel, C. T. Poison, L. E. Barber, I. Bursuker, V. L. Guss, J. A. Corsa, D. M. Barten, K. M. Felsenstein, S. B. Roberts, Bioorg. Med. Chem. Lett. 2008, 18, 175-178.
34. a) A. R. Katritzky, B. V. Rogovoy, K. V. Kovalenko, J. Org. Chem. 2003, 68, 4941-4943;
35. b) W L. Garbrecht, R. M. Herbst, J. Org. Chem. 1953, 18, 1003-1013;
36. c) S. Kamijo, Z. Huo, T. Jin, C. Kanazawa, Y. Yamamoto, J. Org. Chem. 2005, 70, 6389-6397.
37. a) Y. Gao, C. Ye, B. Twamley, J. M. Shreeve, Chem. Eur. J. 2006, 12, 9010-9018;
38. b) E. V. Tretyakov, G. V. Romanenko, V. I. Ovcharenko, Tetrahedron 2004, 60, 99-103.
39. a) Z. Zeng, W. S. Hyer, B. Twamley, J. M. Shreeve, Synthesis 2008, 1775-1782;
40. b) Z. Zeng, R. Wang, B. Twamley, D.A. Parrish, J. M. Shreeve, Chem. Mater. 2008, 20, 6176-6182.
41. a) M. Hesse, H. Meier, B. Zeeh, Spektroskopische Methoden in der organischen Chemie, vol. 7, Georg Thieme Verlag, Stuttgart, New York, 2005;
42. 15N-NMR-Spektroskopie, Georg Thieme Verlag, Stuttgart, New York, 1992, pp. 36-38;
43. c) A. M. Orendt, J. Michl, J. Reiter, Magn. Reson. Chem. 1989, 27, 1-3.
44. a) L. Huff, D. M. Forkey, D. W. Moore, R. A. Henry, J. Org. Chem. 1970, 35, 2074-2076;
45. b) G. B. Ansell, J. Chem. Soc, C 1970, 684;
46. c) H. Hori, M. Fujii, Y. Shiro, T. Iizuka, S. Adachi, I. Morishima, J. Biol. Chem. 1989, 264, 5715-5719.
47. a) APEX2 v2.1-0, Bruker AXS Inc., Madison, Wisconsin, USA, 2006;
48. b) SAINT v7.34A, Bruker AXS Inc., Madison, Wisconsin, USA, 2005;
49. c) XPREP v2005/2, Bruker AXS Inc., Madison, Wisconsin, USA, 2004;
50. d) SADABS v2004/l, Bruker AXS Inc., Madison, Wisconsin, USA, 2004;
51. e) SHELXTL v6.12, Bruker AXS Inc., Madison, Wisconsin, USA, 2000.