Radical deoxygenation of 3-azatricyclo[2.2.1.02,6]heptan-5-ols to 1,2-dihydropyridines

Synlett

Volumn , Issue 2, 2005, Pages 325-327

  Hodgson, David M ^a   Jones, Matthew L ^a   Maxwell, Christopher R ^a   Ichihara, Osamu ^b   Matthews, Ian R ^c  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b EVOTEC UK LTD   (United Kingdom)

^c JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

Author keywords

Alcohols; Deoxygenation; Dihydropyridines; Free radicals; Rearrangements

Indexed keywords

1 TOSYL 3 AZATRICYCLO[2.2.1.0 2,6]HEPTAN 5 OL; 1,2 DIHYDROPYRIDINE; 3 AZATRICYCLO[2.2.1.0 2,6]HEPTAN 5 OL; 4 TOSYL 2 AZABICYCLO[2.2.1]HEPT 5 ENE; 5 TOSYL 1,2 DIHYDROPYRIDINE; ALCOHOL DERIVATIVE; DIHYDROPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DEOXYGENATION; REACTION ANALYSIS; SYNTHESIS;

EID: 13844250295     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-836066     Document Type: Article

References (23)

1. (a) Beckwith, A. L. J.; Ingold, K. U. In Rearrangements in Ground and Excited States, Vol. 1; de Mayo, P., Ed.; Academic: New York, 1980, 161.
2. (b) Giese, B.; Kopping, B.; Göbel, T.; Dickhaut, J.; Thoma, G.; Kulicke, K. J.; Trach, F. Org. React. 1996, 48, 301.
3. (c) Radicals in Organic Synthesis; Renaud, P.; Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001.
4. (a) Warner, C. R.; Strunk, R. J.; Kuivila, H. G. J. Org. Chem. 1966, 31, 3381.
5. (b) Halgren, T. A.; Firkins, J. L.; Fujimoto, T. A.; Suzukawa, H. H.; Roberts, J. D. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 3216.
6. Hodgson, D. M.; Maxwell, C. R.; Wisedale, R.; Matthews, I. R.; Carpenter, K. J.; Dickenson, A. H.; Wonnacott, S. J. J. Chem. Soc., Perkin Trans. 1 2001, 3150.
7. Hodgson, D. M.; Bebbington, M. W. P.; Willis, P. Org. Biomol. Chem. 2003, 1, 3787.
8. Jin, Z.; Fuchs, P. L. J. Am. Chem. Soc. 1995, 117, 3022.
9. Afarinkia, K.; Mahmood, F. Tetrahedron Lett. 2000, 41, 1287.
10. CCDC 237474 available at http://www.ccdc.cam.ac.uk.
11. Crich, D.; Quintero, L. Chem. Rev. 1989, 89, 1413.
12. No 1,2-dihydropyridines 12 were observed as by-products from these reactions.
13. (a) Dieter, R. K.; Sharma, R. R. J. Org. Chem. 1996, 61, 4180.
14. (b) McDonald, F. E.; Chatterjee, A. K. Tetrahedron Lett. 1997, 38, 7687.
15. 4) in 43% and 59% yields, respectively.
16. 4]: 473.2098.
17. (b) Curran, D. P.; Chang, C.-T. J. Org. Chem. 1989, 54, 3140.
18. 4).
19. Zhang, C.; Izenwasser, S.; Katz, J. L.; Terry, P. D.; Trudell, M. L. J. Med. Chem. 1998, 41, 2430.
20. Zhang, C.; Trudell, M. L. J. Org. Chem. 1996, 61, 7189.
21. For a recent review on dihydropyridines, see: Lavilla, R. J. Chem. Soc., Perkin Trans. 1 2002, 1141.
22. Buolamwini, J. K.; Knaus, E. E. Eur. J. Med. Chem. 1993, 447.
23. Leung-Toung, R.; Liu, Y.; Muchowski, J. M.; Wu, Y.-L. J. Org. Chem. 1998, 63, 3235.