Copper-catalyzed intramolecular dehydrogenative aminooxygenation: Direct access to formyl-substituted aromatic N-heterocycles

Angewandte Chemie - International Edition

Volumn 50, Issue 25, 2011, Pages 5678-5681

  Wang, Honggen ^a   Wang, Yong ^a   Liang, Dongdong ^a   Liu, Lanying ^a   Zhang, Jiancun ^a   Zhu, Qiang ^a  

^a GUANGZHOU INSTITUTES OF BIOMEDICINE AND HEALTH   (China)

Author keywords

aldehydes; aminooxygenation; dehydrogenation; N heterocycles; synthetic methods

Indexed keywords

AMINOOXYGENATION; CARBALDEHYDES; CARBONYL OXYGEN ATOMS; CATALYTIC AMOUNTS; COPPER (II); DIRECT ACCESS; DIRECT SYNTHESIS; MECHANISTIC STUDIES; N-HETEROCYCLES; OXYGEN ACTIVATIONS; PROCESS USE; SYNTHETIC METHODS;

ALDEHYDES; ORGANIC COMPOUNDS; OXYGEN;

COPPER;

ALDEHYDE; COPPER; HETEROCYCLIC COMPOUND; OXYGEN;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION;

ALDEHYDES; CATALYSIS; COPPER; CYCLIZATION; HETEROCYCLIC COMPOUNDS; OXYGEN;

EID: 79958257602     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201100362     Document Type: Article

References (53)

1. For reviews of aminohydroxylation, see H. C. Kolb, M. S. VanNieuwenhze, K. B. Sharpless, Chem. Rev. 1994, 94, 2483
2. D. Nilov, O. Reiser, Adv. Synth. Catal. 2002, 344, 1169
3. J. A. Bodkin, M. D. McLeod, J. Chem. Soc. Perkin Trans. 1 2002, 2733
4. K. Muniz, Chem. Soc. Rev. 2004, 33, 166.
5. For recent examples of aminoacetoxylation and aminobenzoxylation, see, D. E. Mancheno, A. R. Thornton, A. H. Stoll, A. Kong, S. B. Blakey, Org. Lett. 2010, 12, 4110.
6. For recent examples of aminoalkoxylation, see D. V. Liskin, P. A. Sibbald, C. F. Rosewall, F. E. Michael, J. Org. Chem. 2010, 75, 6294
7. P. Szolcsanyi, T. Gracza, Chem. Commun. 2005, 3948
8. P. H. Fuller, J.-W. Kim, S. R. Chemler, J. Am. Chem. Soc. 2008, 130, 17638.
9. Ś. Albrecht, H. Jiang, G. Dickmeiss, B. Gschwend, S. G. Hansen, K. A. Jørgensen, J. Am. Chem. Soc. 2010, 132, 9188
10. C. Stephen, Tetrahedron 2000, 56, 2561.
11. The formation of oxygen-containing heterocycles through intramolecular aminooxygenation is less common. For recent examples, see L. V. Desai, M. S. Sanford, Angew. Chem. 2007, 119, 5839
12. Angew. Chem. Int. Ed. 2007, 46, 5737
13. J. M. Mahoney, C. R. Smith, J. N. Johnston, J. Am. Chem. Soc. 2005, 127, 1354.
14. E. J. Alexanian, C. Lee, E. J. Sorensen, J. Am. Chem. Soc. 2005, 127, 7690
15. P. Szolcsanyi, T. Gracza, Chem. Commun. 2005, 3948.
16. M. C. Paderes, S. R. Chemler, Org. Lett. 2009, 11, 1915.
17. K. S. Williamson, T. P. Yoon, J. Am. Chem. Soc. 2010, 132, 4570.
18. T. J. Donohoe, G. H. Churchill, K. M. P. Wheelhouse, P. A. Glossop, Angew. Chem. 2006, 118, 8193
19. Angew. Chem. Int. Ed. 2006, 45, 8025
20. T. J. Donohoe, M. J. Chughtai, D. J. Klauber, D. Griffin, A. D. Campbell, J. Am. Chem. Soc. 2006, 128, 2514
21. T. J. Donohoe, C. J. R. Bataille, W. Gattrell, J. Kloesges, E. Rossignol, Org. Lett. 2007, 9, 1725
22. T. J. Donohoe, C. K. A. Callens, A. L. Thompson, Org. Lett. 2009, 11, 2305.
23. Chiba reported a similar example of dehydrogenative intramolecular aminooxygenation as a side reaction of the copper-catalyzed synthesis of azaspirocyclohexadienones, see:, S. Chiba, L. Zhang, J.-Y. Lee, J. Am. Chem. Soc. 2010, 132, 7266.
24. A. R. Katritzky, Y.-J. Xu, H. Tu, J. Org. Chem. 2003, 68, 4935, and references therein.
25. N. Chernyak, V. Gevorgyan, Angew. Chem. 2010, 122, 2803
26. Angew. Chem. Int. Ed. 2010, 49, 2743.
27. H. Wang, Y. Wang, C. Peng, J. Zhang, Q. Zhu, J. Am. Chem. Soc. 2010, 132, 13217.
28. For a multistep synthesis of imidazo[1,2-a]pyridine-3-carbaldehydes, see L. Almirante, A. Mugnaini, N. D. Toma, A. Gamba, W. Murmann, J. Hidalgo, J. Med. Chem. 1970, 13, 1048
29. C. E. McKenna, et al., J. Med. Chem. 2010, 53, 3454, see the Supporting Information for the full citation.
30. A. R. Katritzky, A. F. Pozharskii, Handbook of Heterocyclic Chemistry, 2nd ed., Pergamon, Amsterdam, 2000
31. L. De Luca, Curr. Med. Chem. 2006, 13, 1.
32. For recent examples of imidazole synthesis, see, L. Liu, M. Frohn, N. Xi, C. Dominguez, R. Hungate, P. J. Reider, J. Org. Chem. 2005, 70, 10135
33. A. V. Gulevich, E. S. Balenkova, V. G. Nenajdenko, J. Org. Chem. 2007, 72, 7878
34. R. B. Sparks, A. P. Combs, Org. Lett. 2004, 6, 2473
35. S. Zaman, K. Mitsuru, A. D. Abell, Org. Lett. 2005, 7, 609.
36. J. Kerhervé, C. Botuha, J. Dubois, Org. Biomol. Chem. 2009, 7, 2214
37. B. L. Eriksen, P. Vedsø, M. Begtrup, J. Org. Chem. 2001, 66, 8344
38. C. Madsen, A. A. Jensen, T. Liljefors, U. Kristiansen, B. Nielsen, C. P. Hansen, M. Larsen, B. Ebert, B. Bang-Andersen, P. Krogsgaard-Larsen, B. Frølund, J. Med. Chem. 2007, 50, 4147
39. B. H. Lipshutz, B. Huff, W. Hagen, Tetrahedron Lett. 1988, 29, 3411.
40. M. Webel, A. M. Palmer, C. Scheufler, D. Haag, B. Müller, Org. Process Res. Dev. 2008, 12, 1170.
41. For preparation of substrates 1 and 4, see the Supporting Information.
42. 2
43. C. Zhang, N. Jiao, J. Am. Chem. Soc. 2010, 132, 28
44. L. Huang, H. Jiang, C. Qi, X. Liu, J. Am. Chem. Soc. 2010, 132, 17652.
45. For details in optimizing the reaction conditions, see the Supporting Information.
46. W. C. Pringle, J. M. Peterson, L. Xie, P. Ge, Y. Gao, J. W. Ochterski, J. Lan, WO2006/089076, 2006
47. E. Dubost, D. Le Nouen, J. Streith, C. Tarnus, T. Tschamber, Eur. J. Org. Chem. 2006, 610
48. E. Dubost, T. Tschamber, J. Streith, Tetrahedron Lett. 2003, 44, 3667.
49. J. P. Sauvanet, S. Z. Langer, Imidazopyridines in Sleep Disorders: A Novel Experimental and Therapeutic Approach, L. E. R. S. Monograph Series, Vol. 6 (Ed.:, P. L. Morselli,) Raven Press, New York, 1988.
50. H. Depoortere, P. George, US 5064836, 1991.
51. A mechanism invovling initial formation of aminyl radical is unlikely, see:, O. B. H. Ila, H. Junjappa, J. Org. Chem. 2000, 65, 1583.
52. C. J. Cramer, W. B. Tolman, Acc. Chem. Res. 2007, 40, 601
53. P. J. Donoghue, A. K. Gupta, D. W. Boyce, C. J. Cramer, W. B. Tolman, J. Am. Chem. Soc. 2010, 132, 15869, and references therein.