Synthesis of fused triazole-piperidinoses: A free radical cyclization approach

Tetrahedron Letters

Volumn 41, Issue 3, 2000, Pages 381-384

  Marco Contelles, José ^a   Rodríguez Fernández, Mercedes ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Azole piperidinoses; Free radicals; Glycosidase inhibitors; Triazoles

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; PIPERIDINE DERIVATIVE; TOLUENE; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; METHODOLOGY; MOLECULAR DYNAMICS; SYNTHESIS;

EID: 0343750682     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01981-4     Document Type: Article

References (26)

1. Ermett, P.; Vasella, A. Helv. Chim. Acta 1991, 74, 2043.
2. Krülle, T. M.; de la Fuente, C.; Pickering, L.; Aplin, R. T.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Nash, R. J.; Griffiths, R. C.; Fleet, G. W. J. Tetrahedron: Asymmetry 1997, 8, 3807.
3. Aoyama, T.; Naganawa, H.; Suda, H.; Uoptani, K.; Aoyagi, T.; Takeuchi, T. J. Antibiot. 1992, 45, 1557.
4. Elbein, A. D. Ann. Rev. Biochem. 1987, 56, 497.
5. Bols, M. Acc. Chem. Res. 1998, 31, 1.
6. Frankowski, A.; Deredas, D.; Streith, J.; Tschamber, T. Tetrahedron 1998, 54, 9033.
7. Granier, T.; Gaiser, F.; Hintermann, L.; Vasella, A. Helv. Chim. Acta 1997, 80, 1443.
8. (a) Majumdar, S.; Bhattacharjya, A.; Patra, A. Tetrahedron Lett. 1997, 38, 8581;
9. (b) Czernecki, S.; Ayadi, E.; Xie, J. Tetrahedron Lett. 1996, 37, 9193;
10. (c) Xi, Z.; Glemarec, C.; Chattopadhyaya, C. Tetrahedron 1993, 49, 7525.
11. For free radical cyclization on conveniently functionalized indoles, see: (a) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (b) Ziegler, F. E.; Harran, P. G. J. Org. Chem. 1993, 58, 2768. For imidazoles and benzimidazoles, see: (c) Aldabbagh, F.; Bowman, W. R. Tetrahedron Lett. 1997, 38, 3793; (d) Aldabbagh, F.; Bowman, W. R. Tetrahedron 1999, 55, 4109. For pyrroles, see: (e) Aldabbagh, F.; Bowman, W. R.; Mann, E. Tetrahedron Lett. 1997, 38, 7937.
12. For free radical cyclization on conveniently functionalized indoles, see: (a) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (b) Ziegler, F. E.; Harran, P. G. J. Org. Chem. 1993, 58, 2768. For imidazoles and benzimidazoles, see: (c) Aldabbagh, F.; Bowman, W. R. Tetrahedron Lett. 1997, 38, 3793; (d) Aldabbagh, F.; Bowman, W. R. Tetrahedron 1999, 55, 4109. For pyrroles, see: (e) Aldabbagh, F.; Bowman, W. R.; Mann, E. Tetrahedron Lett. 1997, 38, 7937.
13. For free radical cyclization on conveniently functionalized indoles, see: (a) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (b) Ziegler, F. E.; Harran, P. G. J. Org. Chem. 1993, 58, 2768. For imidazoles and benzimidazoles, see: (c) Aldabbagh, F.; Bowman, W. R. Tetrahedron Lett. 1997, 38, 3793; (d) Aldabbagh, F.; Bowman, W. R. Tetrahedron 1999, 55, 4109. For pyrroles, see: (e) Aldabbagh, F.; Bowman, W. R.; Mann, E. Tetrahedron Lett. 1997, 38, 7937.
14. For free radical cyclization on conveniently functionalized indoles, see: (a) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (b) Ziegler, F. E.; Harran, P. G. J. Org. Chem. 1993, 58, 2768. For imidazoles and benzimidazoles, see: (c) Aldabbagh, F.; Bowman, W. R. Tetrahedron Lett. 1997, 38, 3793; (d) Aldabbagh, F.; Bowman, W. R. Tetrahedron 1999, 55, 4109. For pyrroles, see: (e) Aldabbagh, F.; Bowman, W. R.; Mann, E. Tetrahedron Lett. 1997, 38, 7937.
15. For free radical cyclization on conveniently functionalized indoles, see: (a) Moody, C. J.; Norton, C. L. Tetrahedron Lett. 1995, 36, 9051; (b) Ziegler, F. E.; Harran, P. G. J. Org. Chem. 1993, 58, 2768. For imidazoles and benzimidazoles, see: (c) Aldabbagh, F.; Bowman, W. R. Tetrahedron Lett. 1997, 38, 3793; (d) Aldabbagh, F.; Bowman, W. R. Tetrahedron 1999, 55, 4109. For pyrroles, see: (e) Aldabbagh, F.; Bowman, W. R.; Mann, E. Tetrahedron Lett. 1997, 38, 7937.
16. For some isolated examples, in the nucleoside area, see: (a) Sugawara, T.; Otter, B. A.; Ueda, T. Tetrahedron Lett. 1988, 29, 75;(b) Ueda, T.; Shuto, S. Nucleosides Nucleotides 1984, 3, 295.
17. For some isolated examples, in the nucleoside area, see: (a) Sugawara, T.; Otter, B. A.; Ueda, T. Tetrahedron Lett. 1988, 29, 75;(b) Ueda, T.; Shuto, S. Nucleosides Nucleotides 1984, 3, 295.
18. The synthesis of the radical precursors will be reported elsewhere.
19. (a) Giese, B. Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds; Pergamon Press, New York, 1986.
20. (b) Motherwell, W. B.; Crich, D. Free Radical Chain Reactions in Organic Synthesis; Academic Press, London, 1992.
21. 2O], 24.2 (C6).
22. In these cases, traces of the reduced, uncyclized derivatives 6b and 8b (Scheme 2) were detected.
23. (a) Curran, D. P.; Yu, H.; Liu, H. Tetrahedron 1994, 50, 7343. See also:
24. (b) Antonio, Y.; de la Cruz, M. E.; Galeazzi, E.; Guzmán, A.; Bray, B. L.; Greenhouse, R.; Kurz, L. J.; Lustig, D. A.; Maddox, M. L.; Muchowski, J. M. Can. J. Chem. 1994, 72, 15;
25. (c) Rosa, A. M.; Lobo, A. M.; Branco, P. S.; Prabhakar, S.; Pereira, A. M. D. L. Tetrahedron 1997, 53, 269.
26. The authors thank the referee for this suggestion.