Ring expansions of 1-azabicyclo[n.1.0]alkanes. Recent developments

Arkivoc

Volumn 2011, Issue 1, 2011, Pages 329-345

  Tymoshenko, Dmytro O ^a  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

1 Azabicyclo n.1.0 alkanes; Aziridine; Aziridinium; Ring expansion

Indexed keywords

EID: 80051737105     PISSN: 1551-7012     EISSN: 15517004     Source Type: Journal    
DOI: 10.3998/ark.5550190.0012.105     Document Type: Review

References (56)

1. (a) Bremner, J. B. In Progress in Heterocyclic Chemistry; Gribble, G. W.; Joule, J. A. Eds.; Elsevier: Oxford, 2004; Vol. 16, p 431.
2. (b) Bremner, J. B. In Progress in Heterocyclic Chemistry; Gribble, G. W.; Joule, J. A. Eds.; Elsevier: Oxford, 2005; Vol. 17, p 389.
3. (c) Quirion, J.-C.; Leclerc, E.; Jubault, P. In Science of Synthesis, Houben-Weyl Methods of Organic Transformations; Molander, G., Ed.; Georg Thieme Verlag: Stuttgart, 2007; Vol. 20, p 659.
4. (d) Fraser, H. L.; Floyd, M. B.; Hopper, D. W. In Progress in Heterocyclic Chemistry; Gribble, G. W.; Joule, J. A. Eds.; Elseveir: Oxford, 2007; Vol. 18, p 310.
5. Kaellstroem, S.; Leino, R. Bioorg. Med. Chem. 2008, 16, 601.
6. (a) Companyo, X.; Alba, A.-N.; Rios, R. Targets Heterocycl. Syst. 2009, 13, 147.
7. (b) Troin, Y.; Sinibaldi, M.-E. Targets Heterocycl. Syst. 2009, 13, 120.
8. Wahba, A. E.; Hamann, M. T. Marine Drugs 2010, 8, 2395.
9. (a) Merino, P.; Delso, I.; Marca, E.; Tejero, T.; Matute, R. Curr. Chem. Biology 2009, 3, 253.
10. (b) Vogel, P.; Gerber-Lemaire, S.; Juillerat-Jeanneret, L. In Iminosugars Compain, P.; Martin, O. R. Eds.; John Wiley and Sons 2007, 87.
11. Koulocheri, S. D.; Pitsinos, E. N.; Haroutounian, S. A. Curr. Org. Chem. 2008, 12, 1454.
12. Yamashita, Y.; Kobayashi, S. In Handbook of Cyclization Reactions Ma, S., Ed.; Wiley, Inc. 2010, Vol. 1, p 59.
13. Katritzky, A. R.; Rachwal, S. Chem. Rev. 2010, 110, 1564.
14. (a) Vicario, J. L.; Badia, D.; Carrillo, L.; Ruiz, N.; Reyes, E. Targets Heterocycl. Syst. 2008, 12, 302.
15. (b) 2009MI139 Troin, Y.; Sinibaldi, M.-E. In Synthesis of Nitrogen Heterocycles, Royer, J. Ed.; Wiley-VCH Verlag GmbH and Co KGaA: Weinheim, 2009, 139.
16. Remuson, R.; Gelas-Mialhe, Y. Mini-Reviews Org. Chem. 2008, 5, 193.
17. (a) Cossy, J.; Pardo, D. G. Chemtracts 2002, 15, 579.
18. (b) Cossy, J.; Pardo, D. G. Targets Heterocycl. Syst. 2002, 6, 1.
19. Pearson, W. H.; Lian, B. W. In Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees, E. F. V. Scriven, Eds.; Pergamon: Oxford, 1996, vol. 1, p 1.
20. Joucla, M.; Fouchet, B.; Hamelin, J. Tetrahedron 1985 41, 2707.
21. (a) Couty, F.; Durrat, F.; Prim, D. Tetrahedron Lett. 2003, 44, 5209.
22. (b) Durrat, F.; Sanchez, M. V.; Couty, F.; Evano, G.; Marrot, J. Eur. J. Org. Chem. 2008, 19, 3286.
23. Drouillat, B.; Couty, F.; David, O.; Evano, G.; Marrot, J. Synlett 2008, 9, 1345.
24. R. C. Fuson, C. L. Zirkle, J. Am. Chem. Soc. 1948, 70, 2760.
25. (a) Roudeau, R.; Pardo, D. G.; Cossy, J. Tetrahedron 2006, 62, 2388.
26. (b) Brandi, A.; Cicchi, S.; Paschetta, V.; Pardo, D. G.; Cossy, J. Tetrahedron Lett. 2002, 43, 9357.
27. (c) Lonkar, P. S.; Kumar, V. A. Bioorg. Med. Chem. Lett. 2004, 14, 2147.
28. Heindl, C.; Hubner, H.; Gmeiner, P. Tetrahedron: Asymmetry 2003, 14, 3153.
29. D'hooghe, M.; Baele, J.; Contreras, J.; Boelens, M.; De Kimpe, N. Tetrahedron Lett. 2008, 49, 6039.
30. Mena, M.; Bonjoch, J.; Gomez-Pardo, D.; Cossy, J. J. Org. Chem. 2006, 71, 5930.
31. (a) Dechamps, I.; Pardo, D. G.; Cossy, J. Synlett 2007, 263.
32. (b) Dechamps, I.; Pardo, D. G.; Cossy, J. Eur. J. Org. Chem. 2007, 4224.
33. Dechamps, I.; Pardo, D. G.; Cossy, J. Tetrahedron 2007, 63, 9082.
34. Ori, M.; Toda, N.; Takami, K.; Tago, K.; Kogen, H. Tetrahedron 2005, 61, 2075.
35. Deyine, A.; Delcroix, J.-M.; Langlois, N. Heterocycles 2004, 64, 207.
36. Dondoni, A.; Richichi, B.; Marra, A.; Perrone, D. Synlett 2004, 1711.
37. Cossy, J.; Mirguet, O.; Pardo, D.G.; Desmurs, J.-R. Tetrahedron Lett. 2001, 42, 5705.
38. Cossy, J.; Mirguet, O.; Pardo, D. G.; Desmurs, J.-R. Eur. J. Org. Chem. 2002, 3543.
39. Brown, D.; Brown, G. A.; Andrews, M.; Large, J. M.; Urban, D.; Butts, C. P.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 2002, 17, 2014.
40. (a) Khlebnikov, A. F.; Novikov, M. S.; Amer, A. A. Russ. Chem. Bull, Int. Ed. 2004 53, 1092.
41. (b) Khlebnikov, A. F.; Novikov, M. S.; Amer, A. A. Tetrahedron Lett. 2002, 43, 8523.
42. Beduerftig, S.; Wuensch, B. Eur. J. Med. Chem. 2006, 41, 387.
43. Fesenko, A. A.; Tullberg, M. L.; Shutalev, A. D. Tetrahedron 2009, 65, 2344.
44. Shinkevich, E. Yu.; Novikov, M. S.; Khlebnikov, A. F. Synthesis 2007, 225.
45. Alves, M. J.; Fortes, A. G.; Costa, F. T.; Duarte, V. C. M. Tetrahedron 2007, 63, 11167.
46. Alves, M. J.; Gilchrist, T. L. Tetrahedron Lett. 1998, 39, 7579.
47. Ducray, R.; Cramer, N.; Ciufolini, M. A. Tetrahedron Lett. 2001, 42, 9175.
48. Ducray, R; Ciufolini, M. A. Angew. Chem. Int. Ed. 2002, 41, 4688.
49. Davies, S. G.; Nicholson, R. L.; Price, P. D.; Roberts, P. M.; Smith, A. D. Synlett 2004, 901.
50. Verhelst, S. H. L.; Martinez, B. P.; Timmer, M. S. M.; Lodder, G.; van der Marel, G. A.; Overkleeft, H. S.; van Boom, J. H. J. Org. Chem. 2003, 68, 9598.
51. (a) Bulanov, M. N.; Sosonyuk, S. E.; Zyk, N. V.; Zefirov, N. S. Russ. J. Org. Chem. (Transl. Zhurn. Org. Khimii) 2003, 39, 415.
52. (b) Krow, G. R.; Gandla, D.; Guo, W.; Centafont, R. A.; Lin, G.; DeBrosse, C.; Sonnet, P. E.; Ross III, C. W.; Ramjit, H. G. Carroll, P. G. Cannon, K. C. J. Org. Chem. 2008, 73, 2114.
53. Gayet, A.; Andersson, P. G. Adv. Synth. Catal. 2005, 347, 1242.
54. Carman, R. M.; Derbyshire, R. P. C. Aust. J. Chem. 2003, 56, 319.
55. (a) Timén, Å. S.; Somfai, P. J. Org. Chem. 2003, 68, 9958.
56. (b) Timén, Å. S.; Fischer, A.; Somfai, P. Chem. Commun. 2003, 1150.