Synthesis of 5-azaindoles via a cycloaddition reaction between nitriles and donor-acceptor cyclopropanes

Organic Letters

Volumn 12, Issue 14, 2010, Pages 3168-3171

  Moustafa, Mahmoud M Abd Rabo ^a   Pagenkopf, Brian L ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

5 AZAINDOLE; 5-AZAINDOLE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; HETEROCYCLIC COMPOUND; INDOLE DERIVATIVE; NITRILE; PIPERIDINE; PIPERIDINE DERIVATIVE; PYRIDINE; PYRIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

AZA COMPOUNDS; CYCLOPROPANES; INDOLES; NITRILES; OXIDATION-REDUCTION; PIPERIDINES; PYRIDINES;

EID: 77954560270     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol101078z     Document Type: Article

References (45)

1. For recent reviews and references cited therein see
2. Popowyez, F.; Mérour, J.-Y.; Joseph, B. J. Tetrahedron 2007, 63, 8689-8707
3. Song, J. J.; Reeves, J. T.; Gallou, F.; Tan, Z.; Yee, N. K.; Senanayake, C. H. Chem. Soc. Rev. 2007, 36, 1120-1132
4. Popowycz, F.; Routier, S.; Joseph, B.; Mérour, J.-Y. Tetrahedron 2007, 63, 1031-1064
5. Bastian, J. A.; Fisher, M. J.; Harper, R. W.; Lin, H.-S.; Mccowan, J. R.; Sall, D. J.; Smith, G. F.; Takeuchi, K.; Wiley, M. R.; Zhang, M. Eur. Pat. Appl. EP 997465, 2000 Chem. Abstr. 2000, 132, 293756
6. Wei, Z.; Dolaine, R.; Walpole, C.; Yang, H. Appl. Int. WO 2004087704, 2004 Chem. Abstr. 2004, 141, 332183
7. Cooper, L. C.; Chicchi, G. G.; Dinnell, K.; Elliott, J. M.; Hollingworth, G. J.; Kurtz, M. M.; Locker, K. L.; Morrison, D.; Shaw, D. E.; Tsao, K.-L.; Watt, A. P.; Williams, A. R.; Swain, C. J. Bioorg. Med. Chem. Lett. 2001, 11, 1233-1036
8. Jinnin, M.; Ihn, H.; Tamaki, K. Mol. Pharmacol. 2006, 69, 597-607
9. Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000, 7, 1045-1075
10. Evans, G. B.; Furneaux, R. H.; Hutchison, T. L.; Kezar, H. S.; Morris, P. E., Jr.; Schramm, V. L.; Tyler, P. C. J. Org. Chem. 2001, 66, 5723-5730
11. Zhu, J.; Wong, H.; Zhang, Z.; Yin, Z.; Meanwell, N. A.; Kadow, J. F.; Wang, T. Tetrahedron Lett. 2006, 47, 5653-5656
12. Roy, P. J.; Dufresne, C.; Lachance, N.; Leclerc, J.-P.; Boisvert, M.; Wang, Z.; Leblanc, Y. Synthesis 2005, 2751-2757
13. Zhang, Z.; Yang, Z.; Meanwell, N. A.; Kadow, J. F.; Wang, T. J. Org. Chem. 2002, 67, 2345-2347
14. Saab, F.; Bénéteau, V.; Schoentgen, F.; Mérour, J.-Y.; Routier, S. Tetrahedron 2010, 66, 102-110
15. Zheng, X.; Kerr, M. A. Org. Lett. 2006, 8, 3777-3779
16. Fang, Y.-Q.; Yuen, J.; Lautens, M. J. Org. Chem. 2007, 72, 5152-5160
17. Roy, P.; Boisvert, M.; Leblanc, Y. Org. Synth. 2007, 84, 262-271
18. Lefoix, M.; Daillant, J.-P.; Routier, S.; Merour, J.-Y.; Gillaizeau, I.; Coudert, G. Synthesis 2005, 20, 3581-3588
19. Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B. Tetrahedron Lett. 1998, 39, 5159-5162
20. Bisagni, E.; Ducrocq, C.; Civier, A. Tetrahedron 1976, 32, 1383-1390
21. Zhang, S.; Sun, X.; Zhang, W.-X.; Xi, Z. Chem. - Eur. J. 2009, 15, 12608-12617
22. Shaykoon, M. S. A.; Inagaki, F.; Mukai, C. Heterocycles 2010, 80, 133-139
23. Whelligan, D. K.; Thomson, D. W.; Taylor, D.; Hoelder, S. J. Org. Chem. 2010, 75, 11-15
24. Yu, M.; Pagenkopf, B. L. J. Am. Chem. Soc. 2003, 125, 8122-8123
25. Yu, M.; Pagenkopf, B. L. Org. Lett. 2003, 5, 5099-5101
26. Yu, M.; Pantos, G. D.; Sessler, J. L.; Pagenkopf, B. L. Org. Lett. 2004, 6, 1057-1059
27. Morra, N. A.; Morales, C. L.; Bajtos, B.; Wang, X.; Jang, H.; Wang, J.; Yu, M.; Pagenkopf, B. L. Adv. Synth. Catal. 2006, 348, 2385-2390
28. Morales, C. L.; Pagenkopf, B. L. Org. Lett. 2008, 10, 157-159
29. Bajtos, B.; Pagenkopf, B. L. Eur. J. Org. Chem. 2009, 1072-1077
30. Reissig, H.-U. Top. Curr. Chem. 1988, 144, 73-135
31. Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151-1196
32. Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321-347
33. Carson, C. A.; Kerr, M. A. Chem. Soc. Rev. 2009, 38, 3051-3060
34. Bridges, T. M.; Brady, A. E.; Kennedy, J. P.; Daniels, R. N.; Miller, N. R.; Kim, K.; Breininger, M. L.; Gentry, P. R.; Brogan, J. T.; Jones, C. K.; Conn, P. J.; Lindsley, C. W. Bioorg. Med. Chem. Lett. 2008, 18, 5439-5442
35. Gassman, P. G.; Burns, S. J. J. Org. Chem. 1988, 53, 5576-5578
36. Charles, R. G. J. Org. Chem. 1957, 22, 677-679
37. Engler, T. A.; Wanner, J. J. Org. Chem. 2000, 65, 2444-2457
38. Benzyl protecting group was first selected to allow for an easy deprotection in the subsequent oxidation step.
39. Both diastereomers work equally well in the subsequent cyclization.
40. Harrison, D. M.; Sharma, R. B. Tetrahedron Lett. 1986, 27, 521-524
41. Becker, M. H.; Chua, P.; Downham, R.; Douglas, C. J.; Garg, N. K.; Hiebert, S.; Jaroch, S.; Matsuoka, R. T.; Middleton, J. A.; Ng, F. W.; Overman, L. E. J. Am. Chem. Soc. 2007, 129, 11987-12002
42. Wallace, D. J.; Gibb, A. D.; Cottrell, I. F.; Kennedy, D. J.; Brands, K. M. J.; Dolling, U. H. Synthesis 2001, 12, 1784-1789
43. Bagley, M. C.; Lubinu, M. C. Synthesis 2006, 8, 1283-1288
44. Gatta, F.; Misiti, D. J. Heterocycl. Chem. 1987, 24, 1183-1187
45. Bajtos, B.; Yu, M.; Zhao, H.; Pagenkopf, B. L. J. Am. Chem. Soc. 2007, 129, 9631-9634